THE PORPHYRINS Volume I Structure and Synthesis, Part A Edited by DAVID DOLPHIN Department of Chemistry University of British Columbia Vancouver, British Columbia, Canada ACADEMIC PRESS New York San Francisco London A Subsidiary of Harcourt Brace Jovanovich, Publishers
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THE PORPHYRINS Volume I
Structure and Synthesis, Part A
Edited by
DAVID DOLPHIN Department of Chemistry
University of British Columbia Vancouver, British Columbia, Canada
A C A D E M I C P R E S S New York San Francisco London
A Subsidiary of Harcourt Brace Jovanovich, Publishers
Contents
1 Nomenclature
R. BONNETT
I. Introduction 2 II. Pyrroles 2
III. Systems with Two Pyrrole Rings 3 IV. Porphyrins and Related Compounds: The Fischer Nomenclature 4 V. Porphyrins and Related Compounds: A Revised Nomenclature 9
VI. Linear Tri- and Tetrapyrroles 14 VII. Ring-Contracted and Ring-Expanded Systems 19
VIII. Metal Complexes 21 References 26
2 Selected Landmarks in the History of Porphyrins and Their Biologically Functional Derivatives
DAVID L. DRABKIN
I- Challenge of Disease States 31 II. Thudichum's Cruentine (Hematoporphyrin) 34
III. Experimental Disease States 36
IV. Important Books, Monographs, and Reviews 38 V. Conferences, Symposia, and Colloquia 40
VI. Determination of Iron Content of Hemoglobin (A Standard for Hemoglobinometry) 52
VII. Crystallization of Porphyrins, Hemes, and Hemoproteins 55 VIII. Hemochromogens 55
IX. Continuum of Concepts 61
X. Ongoing Problems: Return to the Functional Environment of the Cell 69
XI. Concluding Remarks 69 XII. Addendum 71
References 71
3 Synthesis of Porphyrins from Monopyrroles
JEAN B. KIM, A L A N D. ADLER, AND FREDERICK R. LONGO
I. Synthesis of Porphin and Chlorin 85 II. Synthesis of b-Substituted Porphyrins 87
III. Synthesis of meso-Substituted Porphyrins 88 IV. Mechanistic Considerations 90 V. Cis, Trans-Dipyrrylmethene and Polypyrrylmethene Precursors 95
VI. Substituent Effects 96 VII. Cyclic Tetrapyrrole Intermediates 97
VIII. Conclusion 99 References 99
4 Synthesis of Pyrroles and of Porphyrins via Single-Step Coupling of Dipyrrolic Intermediates
JOHN B. PAINE III
I. Synthesis of Pyrroles from Acyclic Precursors 101 II. Manipulations of Monopyrrolic Porphyrin Precursors:
Transformation of a-Substituents of 5-Methylpyrrole-2-Carboxylic Esters 135
III. Synthesis of Dipyrrolic Intermediates and Their Conversion to Porphyrins 163
IV. Appendix: Selected Examples of 2 + 2 Porphyrin Syntheses 224 References 231
5 Synthesis of Porphyrins from 1,19-Dideoxybiladienes-ac and 1,19-Dideoxybilenes-A
A. W. JOHNSON
I. Introduction 235 II. Linear Tetrapyrroles 237
References 263
6 Synthesis of Porphyrins from Oxobilane Intermediates
P. S. CLEZY AND A. H. JACKSON
I. Introduction 265 II. Dipyrroketones 266
III. Porphyrins from a-Oxobilanes 269 IV. Porphyrins from b-Oxobilanes 274 V. Differential Protection of Pyrrole Rings 279
VI. Synthesis of Porphyrins Bearing Labile Groups 280 VII. Conclusions 284
References 286
7 Isolation and Modification of Natural Porphyrins
ROBERT K. DINELLO AND C. K. CHANG
I. Introduction 290 II. Protoporphyrin and Related Natural Porphyrin Derivatives 290
III. Porphyrins Derived from Degradation of Chlorophylls 324 IV. Interconversion of Porphyrins by Chemical Means 329
References 334
8 N-Substituted Porphyrins and Corroles
A . H . JACKSON
I. N-Substituted Octaalkylporphyrins 341 II. N-Methylated Octaethylchlorins 352
III. N-Alkyl-meso-Tetraphenylporphyrins 354 IV. N-AIkylcorroles 357 V. N-Acetylcorroles 361
VI. Conclusions 362 References 363
9 Azaporphyrins
A. H. JACKSON
I. Introduction 365 II. Monoazaporphyrins 365
III. Diazaporphyrins 369 IV. Tetraazaporphyrins (Porphyrazines) 370 V. Phthalocyanines 374
VI . Analogues of the Phthalocyanines 380 VII. Mono-, Di-, and Triazabenzoporphyrins Related to
Phthalocyanines 383 References 387
10 Synthesis and Properties of Metalloporphyrins
JOHANN WALTER BUCHLER
I. Introduction 390 II. General Considerations 395
III. Central Metals of Group la (Alkali Metals) 424 IV. Central Metals of Groups Ha and l ib (Alkaline Earth and Zinc
Metals) 425 V. Central Metals of Groups Ilia, Illb, and the Lanthanoids 428
VI . Central Metals of Groups IVa, IVb, Va, and Vb 432 VII. Central Metals of Groups Via and V i l a 440
VIII. Central Metals of Groups V i l l a and lb 447 IX. Postscript 474
References 474
11 Geochemistry of Porphyrins
EARL W. BAKER AND SUSAN E. PALMER
I. Introduction 486 II. Isolation and Fractionation of Geoporphyrins 488
III. Identification Methods 493 IV. Treibs' Scheme 505 V. A Survey of Geoporphyrins: Occurrence and Properties 511
VI . Diagenetic Reactions of Tetrapyrroles 536 VII. Concluding Remarks 545
References 550
12 Chromatography of Porphyrins and Metalloporphyrins
WILLIAM I. WHITE, ROBERT C. BACHMANN, AND BRUCE F. BURNHAM
I. Introduction 553 II. Porphyrins and Metalloporphyrins 559
III. Porphyrin and Metalloporphyrin Esters 565 IV. Synthetic Porphyrins 569 V. Conclusion 574
VI. Addendum 574 References 576
13 Nonchromatographic Methods of Purification of Porphyrins
VERONICA VARADI, FREDERICK R. LONGO, AND A L A N D. ADLER
I. Introduction II. Electrophoresis
581 584
III. Countercurrent Distribution 584 IV. Extraction Methods 584 V. Precipitation and Crystallization 585
VI. Sublimation 586 VII. Miscellaneous 587
VIII. Problems and Future Perspectives 588 References 588
Contributors
A L A N D . A D L E R
ROBERT C . B A C H M A N N
E A R L W . B A K E R
R . B O N N E T T
J O H A N N W A L T E R B U C H L E R
B R U C E F . B U R N H A M
C . K . C H A N G
P . S . C L E Z Y
ROBERT K . D I N E L L O
D A V I D L . D R A B K I N
A . H . JACKSON
A . W . JOHNSON
J E A N B . K I M
F R E D E R I C K R . L O N G O
J O H N B . P A I N E III
S U S A N E . P A L M E R
V E R O N I C A V A R A D I
W I L L I A M I . W H I T E
Author Index
Numbers in parentheses are reference numbers and indicate that an author's work is referred to although his name is not cited in the text. Numbers in italics show the page on which the complete reference is listed.
A
Abd-Elmageed, M. E . , 468(265, 278), 469(265),482, 483
Abeysekera, A. M . , 346( 14b),363 Abraham, R. J . , 345(13),363, 421(112),
Beitchmund, P . , 86, 99 Belcher, R. V . , 283(43), 284(43),288,
561(29), 563(52), 564(52),577 Benesch.R.. 48, 61(171), 76 Benesch.R. E . , 48(171), 61(171), 76 Benson. A . , 292(9),334, 565(71,73,74),
566(74). 578 Ben von. J. H . , 378(49), 388 Berg. H . , 235(2), 263, 299(35),335 Berg. M. H . , 556( 15), 561(27a),577 Bernhart. F. W . , 54, 55(296), £0 Bernstein, S. H . , 61, 62(365),82 Bertin-Sans, H . , 57, 58(325), 59 ,5 / Berzelius, J J , 38, 74 Bessis, M. C , 64, 69(373),82 Beznak. M . , 46(154), 76 Bhatti, M . , 410(62), 429(62), 476,572(122),
579 Bhatti. W. , 410(62), 429(62),476, 572(122),
579 Bickelhaupt, F. ,8(7b),26, 236(6), 238(6),
263, 281(34),287 Billig, M J , 488(20), 491(20), 550 Bilton, J. A . , 381(58),388 Birkhofer, L . , 64(379), 69(379),82 Bischoff H , 58(342), 59 8/ Biswas, K M ,267(12a, 12b), 268( 12a, 12b),
269(l2a, 12b),271(12a, 12b), 286 Blaud, P , 31(33), 72 Bliesener, K. M . , 293(17, 18), 302(45),
Boyle , R , 70(387), 82 Bradbrook, E. F . , 376(42), 381(57),388 Bradley, R . , 298(29),335 Brainerd, F. A . , 30(17), 45(147), 72 Brault, D.,454(225a),4S/ B r a u m a n J . E, 457(232, 232a),481 Braun, A . , 374(32).388 Brauni tzer ,G. ,30,40(109d, 136), 67, 72 , 74,
75 Breger, I. A . , 544(62),551 Brewer, P. , 501(60), 543(60),55/ Brewster, D . , 70(389),83 Brinigar, W. S., 450(203), 454(203),
455(203), 459(241), 480, 482 Broadhurst, M . J . R . , 21(28), 26, 241(19),
Broomfield, S. N . , 375(40),388 Brown, A. P. , 55(310), 70(310),80 Brown, E. B . , 64, 69(374),82 Brown, G. M . , 423(92), 447(92, 164), 448(92,
164), 452(92), 464(92, 164), 465( 164), 477, 479
Brown. H. C, 268( 18), 271(25), 287 Brown , P . M . , 370(\6),387 Brown, S. B . , 454(21 lb),481 B r u c k , S D , 457(233),45/ Brunori , M . , 392(8), 450(8), 454(8), 455(8),
465(8), 466(8), 475 Bubnova, A. G . , 244(29), 262(29),263 B i i c h e r , T \ , 69(383),82 Buchler, J . W . , 43(253-255), 51(253-255),
Buchschacher, P . , 8(7b),26, 236(6), 238(6), 263, 281(34),287
Buckley, D. G . , 574(140), 576(140),580 B u d z i k i e w i e z , H , 422(79),477 B u l l , C , 443(150),479 Bullard, L . , 251(215), 454(215), 262(215),
481 Bullock, E . , 104(5), 122(5), 123(5), 126(5),
Bunnenberg, E . , 44(275), 51(275), 52(275), 79, 80, 423(98),477
Burbidge, P. A . , 541(57),551, 566(79), 570(79), 578
Burger, H . , 422(82), 423(82), 477, 568(19), 578
Burke, J . M . , 423(85),477 Burnham, B. F . , 292, 320(8),334, 406(44),
476 , 554(5), 567(5), 576(145), 576, 580 Burns, R. E . , 538(51),557 B u r w e l l , R . L . , Jr., 457(235),481 Butterfield, E. E . , 53, 55(291),80 Bybnova, A. G . , 244(32),264 Byrne, G. T . , 374(34), 375(34), 377(34),388
C
Caiger, P . , 298(30), 299(30),335 Cajori, F. A . , 30(17), 45(17), 72 Calaveiro, J. A. S., 277(3la), 278(3la, 54,
55), 281(6, 31a)2S7, 288 Calderazzo, F . , 409(51),476 Callot, H. J . , 351(21, 22), 356(23, 27),
357(27), 364 Calvert , C. R . , 565(70),578 Calv in , M , 89, 96(18, 19), 97,99, 100,
Campbell , D. S., 147(68),233 Cannon, R. K . , 52(283), 54(288),£0
Caputo, A . , 39, 40( 109a), 74 Cardinal, R. A . , 566(76), 568(76),578 Carlson. E . G . ,498(22), 550 Carlson, R. E . , 3 18( 114),337, 574(136, 138),
575(136), 576(138),579, 580 Carlton, J . K . , 570(108),579 Carr ,R . P. , 121(34), 217(108),232, 234,
Changeux, J .-P. , 37(97a), 74 Chanutin, A . , 48, 61(170), 76 Chapman, D. J . , 19,26, 558(20),577 Charalambides, A. A . , 450(208), 454(208),
481
Charles, R. G . , 129(47), 130(47),232 Chatterjee, A . , 442( 142), 444( 142), 479 Chen, B. M. L . , 43(257), 51(257), 79 C h e n , M . F . , 107(16), 108(16),231 Cheng, D. O. , 88, 99 Cheung, S. K . , 440( 139), 441( 139),479 Chevrier, B . , 398(25a), 422(25a), 423(25a),
475 Chivvis , A. B . , 43(247), 44(272), 51(247,272),
79, 345(1 \)J63 Chong, R . , 126(43), 146(65), 179(65),
Cohn, E J , 31, 72 C o l e , R . D . , 42(177), 48(177), 77 Cole , W . J . , 19(23),26 Coll ier , G . , 541(57),551 Coll ier , G. L . , 281(37),288, 566(79), 578 Coll ins , D. M . , 425(106), 426(106),478 Coll ins , J . , 322(143),338 Collman, J. P . , 89(32), 100, 450(195, 196,
Conlon, M . , 254(55), 264, 361 (32), 364 Connell , C. R . , 417(72), 432( 128b),
437(l28b), 476 Connelly, J. L . , 311(81), 313(92, 93), J J6 ,
337, 564(64), 578 Conrad, M. E . , 63, 69(370),80, 82 Conway, D C, 569( 102), 579 Cook, A. H . , 39, 40(128), 75, 373(22),387 C o o k s o n , G . H . , 36, 62(86), 74, 267(15),286 Coolidge, E . C , 237(10), 263 Cooper, D. Y.,43(243-245), 50(243-245),
78, 79 Conant, J . B . , 8 , 2 6 Connely, J . , 42(207), 78 Cope, B . T . , 25(31, 32), 27 Corey, R. B . , 30(18), 40( 138), 72, 75 Cornford, P . A. D . , 565(73),578 Corwin , A H , 9,26, 37, 39, 40( 129), 44,
Crosby, W. H . , 63, 69(370),82 Cullen, D. L . , 399(27), 408(27), 425(27),
440(27), 442(27), 446(27), 447(27),475 Cull is , A. F . , 68, 69(382),82 C u r n i s h , R . R . , 48, 61(170), 76
D
D ' A n d r e a , R . W . , 133(51),232 Dandridge, A. G . , 374(31),388 Danieli , G , 37(100), 42( 100), 46( 100), 74 Dannenberg, H . , 313(96),337 Darwin, C , 70(393),83 Das, R. R . , 573(135),579 Datta-Gupta, N . , 89(20), 100, 459(245),
468(270),469(270),482, 572(121), 572(127), 579
Davenport, H . , 309(60),336 Davidson, E. R . , 378(52),388 Davies, H . C , 43(238), 50(238), 78 Davies, J. L . , 195(98), 224(98), 226(98),234 Davies, T. H . , 58(335, 349), 6],81 Davis, D. G . , 423(91), 447(185), 449(185),
472(185), 473(185),477, 480 Davis, J. L . , 3 15(103),337 Dawson, P. J . , 367(7), 368(7),387 Day, R. O . , 442( 144),479 Day, V W , 442(144),479 Dean, R . T . , 576(144),580 Dearden, G. R . , 342(2), 345(2), 346( 15),
347(18), 348(2), 351(2),363, 364 Deasy, C. L . , 42( 174), 48( 174), 77 deC. Hinds, L . , 573(132),579 de Diesback, H . , 374(34),388 tie D u v e , C , 45(148), 76 D e F i l i p p i , L , J , 576(144),550 Degens, E. T . , 505(33), 513(33),550 Deilmann, K. O . , 55(314),50 del C. Battle, A. M . , 565(74), 566(74),578 D e l o r y , G . E . , 54, 55(300),80 Demole, E . , 566(77),578 Dent, C. E . , 375(38, 39), 376(42), 377(44),
384,386,355 Despuy, M. E . , 135(55),232 DeVaux, St. C y r , 58(356),82 D h e r e , C , 4 9 , 77 Diakiw, V . , 105(12),231, 252(51),264,
568(95), 578 Dicker, I. D . , 248(40),264 Diekerson,R. E. ,39,40(109c, 139),
Eaton, W. A . , 417(72), 435(21),476 Eberspaecher, H. I., 459(243).482 Edmonson, P. R . , 320( 128),338 Edsall , J T , 41, 44, 46(142), 76 Efron, M. L . , 67(381), 69(381),82 Eglinton, G . , 486(2), 448( 14), 490( 14),
Elder, G. H . , 224( 113), 225(113),234, 280(32a),257, 318(112), J J7
Eley, D D , 378(49), 388 E l i x , J A , 254(55),264 Ellfolk, N . , 2 9 3 , 295(13),334, 562(39),577 Elliott , W. B . , 52(278), 54(278).80 El l i s , J . , 118(32). 119(32), 123(32), 127(32),
206(32), 231, 254(53), 256(53), 262(53), 264
Ellsworth, R. K . , 503(30, 31), 527(3 I), 550, 569(103), 579
Elsevier, J. O. , 422(81),477 Elson, C. M . , 350(20), 361(32),364 Elvidge, J. A . , 370( 13), 376(13), 380(55, 56),
381(55, 56), 382(55, 59, 60), 387, 388 Enderman, F . , 366(1),387 Engasser ,G. , 573(132).579 Engelhardt, H . . 556( 14), 565( 14), 577 England, M. T . , 321( 135).338, 501(58),
535(58), 541(58),551 English, E. C . , 58(359), 60(359),82 Eplattenier, F. L . , 409(51), 476 Epstein, L. M . , 450 (198), 451( 198),
Fisher. R. G . , 443( 150),479 Fitssimmons, B. W . , 450(208), 454(208),4#/ Fitzgerald, A . , 432( 128a), 434( 128a),478 Flaugh, M. E . , 252(52), 264 Fleischer, E. B . , 50(219), 78, 354(25).
458(226), George, P . , 42, 46, 48(158, 159), 49(186),
67(158), 76, 77, 95(42), 100 Gerald, P. S., 67, 69(381),82 Gewitz , H. S., 311(79), 313(86, 88, 97), JJ6,
337 Giannini , D. D . , 108(19),231 Gibbs, E . , 573(132),579 Gibson, J F , 42( 173), 77 Gibson, K. H . , 111(23). 125(23),231 Gibson, Q H , 42( 172), 48( 172), 77 Gieren, A . , 398(26), 399(26), 436(26),475 Gilchrist , M . , 54(297), 55(297),Stf Gilder, H , 39, 40(108), 74 Gillette, J . , 43(245), 50(245), 79 Glebovskaia, E. A . , 486(3), 507(3), 539(3),
550 Gle im, W . , 3 3 , 7 J , 85,99 Goddard, D. R . , 30, 42, 71 G o e b e K S . , 409(53), 476 Gogan, N. J440(145),479 Goldberg, A . , 32(50), 39, 40(50), 73 Goldberg, D. E . , 351(24a),J64 Golden, J. H . , 380(56), 381(56), 382(60), J&S Goldmacher, J . , 89(34), 100 572(124),579 Gonzalez, B . , 442( 141), 443( 141),479 Goodman, M . M . , 563(55),578 Gore, P. H . , 267(16),286 Gottwald, L. K . , 89(31), 100
G 6 t z , H , 33(63), 73 Gouterman, M . , 43(218), 50(218), 51(249,
Grayson, D. H . , 322(143),338 Green, A . A . , 565(67),578 Green, J. G . , 498(23), 550 Greenlee, W . F . , 108(19),231 Gressl , M . , 43(223), 50(223), 78 Griffith, J. S., 456(228),281 Grigg, R . , 21(27, 28),26, 155(78), 159(78),
438(23a, 24a), 440(23a, 24a),475, 478 Guiodotti , W . , 30(20), 67(20), 72 Gunsalus, I . C , 417(72),476 Giinther, H . , 32, 61(364), 72, 82 Gupta, P . C , 224(111), 225(111),234,
278(32c),280(32c), 287 Gurinovitch, G. P . , 367(8), 369(8),387 Gurinovitch, I. E . , 367(8), 369(8),387 Guryshev, V . N . , 252(48), 256(48),264 Gutman, H. R . , 31(31), 61(31), 72
H
Haagen-Smit, A. J . , 42( 174), 48(174), 77 Haas, 55(311), 56(311),50 Haber l and ,H . , 367(9),387 Haberland, H. W . , 14(19), 15,26 Haberle, N . , 43(262), 79, 88, 95(11), 96, 97,
98,99 Habets, H . , 404(40), 407(40), 423(40),
430(40), 433(40), 436(34), 438(34, 40), 476
H a g e r . L . , 563(46), 577 Hagihara, B . , 55(320, 321, 322), 56(320-
322), 81 Hahn, P. F . , 62(368), 69(368),82 Hai, T. T . , 224( 111), 225(11 \),234, 278(32c),
280(32c), 287 Halbert, T. R . , 89(32), 100, 450(199),
Hartree, E. F . , 30, 36(5), 42, 71, 78 Hauck, F. P . , 8(7b),26, 236(3), 238(6),263,
281(34), 287 Haurowitz, F . , 58(345), 59,81, 440(177),
447( 177), 449( 177) ,473(177), 480 Hausser. K. W . , 49, 77 H a w k e s , G . E.,431(113),478 Hayes, A . , 115(30), 125(30), 126(30),
127(30), 145(30), 174(88), 231, 233, 265(2), 286
Hayes, R. G . , 423(97),477 Hazeldine, D. J . , 378(49),388 Heckmaier, J . , 327(156),338 Heftman, E . , 554(8),576 Heidner, E. L . , 47( 167), 66( 167), 67(167), 76 Helberger, H . , 235(3),263 Helberger, J. H . , 384(61, 62, 63),388 Henderson, L. J . , 39, 40(125), 75 Henderson, R. W . , 566(78),578
Hendry, J. L . , 3 1(34), 72 H e n z i , R . , 409(51),476 Hermanek ,S . 556(11),576 Hernandez, R. , 556(12),576 Hernandez, R., Jr., 556(12),576 Herout, V . , 542(59), 551 Hess, K . , 108(20),231 Hess, P. , 105(11),231 H e v e r , D . B . , 384(63),388 Hilger, J . , 33(67), 75, 319(125),JJS H i l l , H . A . O . , 451(214, 220, 222), 454(214,
220, 222), 457(238), 461(214. 250),481, 482
H i l l , H . C . , 378(49),378 H i l l , R. J . , 30, 30(20), 67, 71, 72 , 309(61),
Jackson, J. R. , 283(43), 284(43),288 Jacob, F.,37(97a),74 Jiiger, P . , 392(9), 409(9),475 J a h n , F . , 54, 55(298),30 Jain, A. C, 1 18(32), 119(32), 123(32),
Jones, R. T. , 70(394),83 Jones, R. V. H . , 242(24), 257(24), 262(24),
263 Jope, H . M . , 54(297), 55(297),80 Jordan, E . , 332,339 j0rgensen,S. K . , 32(51), 73 Jorpes, J. E . , 38(105), 74 Jozefawicz, M. L . , 345(\2),363, 367(7),
K e h l , R . , 559(23), 560(23),577 Keighly, C . , 42(174), 48(174), 77 K e i l i n , J , 358(36), 60,52 Ke i l i n , D , 30, 36(5), 40(132), 42(156),
Kiese, M . , 313(89, 90, 95),336, 337, 564(61), 578
K i m , J. B . , 51(256), 79, 89, 92, 96, 98,100, 408(49), 424(49), 440(49), 441(49), 476, 572(125, 129), 579
K i m , N . , 397(25), 398(25), 422(25), 423(25), 432(25), 433(25), 436(25), 438(25), 440(25), 450( 195), 454(195), 475, 480
K i m , Y C , 125(42), 147(42),232 Kincaid , J.,451(213), 454(213), 459(213),
461(213), King , E J , 54, 55(297),SO K i n g , T E , 43, 50(230), 78 King, T J , 346(14b),363 King, T. L . , 346(14), 358( 14),363
Kirk land , J J 558(17),577 Kirner , J. F . , 442(141), 443( 141), 472(284),
479, 483 Kirshner, W. B . , 88(15), 99 Klarer , J . , 33(71), 73 Kleinspehn, G. G . , 104, 105,231 Klesper. E . , 494(6), 509(6), 518(6), 520(6),
542(6), 550 K l u m p p , T . G . , 54, 55(299),80 Knight, B . C , 292(9),334 Knorr , L . , 102, 108(20), 129,23/ K n o x , K . , 400(32), 401(32), 402(32, 38),
474(38),475, 476 Kobayashi , H . , 378(51),388 Kobert , R . , 43(234), 50(235), 78 K o c h , S., 451(218, 224), 454(218, 224),
460(218, 224),4#/ Koenig, D F , 50(220), 78 K o g l , F , 331(177), 333(177), J J9 Kok i sch , W . , 422(84), 423(84), 447(84),
K o l m , H . G . , 124(39), 167(83),232, 233 K o n , H . , 51(265), 79 K o n d o , T . , 284(51),288 Koningsberg, W . , 30, 67, 72 Korber , E , 38, 40( 115), 58( 1 15), 75 Kornis , G . , 134(53),232 Korsakoff, L . , 89(34), 100, 572(124),579 Kosse l , A , 52(280),SO Kouba , J . , 442( 141), 443( 141), 468(267).
569(101),579 K o z h i c h , D T ,89 ,100 K r a u s , G , 38, 40(117), 75 K r o l , S , 86, 89(4), 96(4), 99 Krzyzanowska , M , 556( 16), 577 K u b y , S A , 55(319), 56,81 K u h n , R . , 49, 64. 69(379), 77, 82, 134(54),
232 Kulkarn i , B D , 206(103), 234 Kunke l , H . G . , 30,42(23, 177),45(23),
46(23), 48(176, 177), 72 , 77 K u r z , H . , 313(89, 90), 336, 564(61), 578 Kurzinger, A . , 249(43),264 Kiister , W . , 33(72), 73, 503(29), 522(29),550 Kvenvolden, K. A . , 44(275), 51(275),
52(275), 79, 80, 521(41), 55/ K w i r a m , A. L . , 43(258), 51(258), 79
L
Labbe, R. F . , 291,334, 562(40),577 Lachman, M . . 299(38),335, 568(90),578 Ladner, J. E . , 47(165, 167), 66(165), 67(165),
47 La Mar , G. N . , 444( 156),261(251), 262(253),
479, 482 Lamson, D. W . , 297(34), 298(33), 313(33),
Langemann, A . , 8(7b),26, 236(6), 238(6), 263, 281(34),287
Lantzke, 1. R . , 454(21 lb),487 Larson, E. A . , 39, 40(130), 75, 462(255),482 Lascelles, J . , 37, 42, 46(98), 74 Laslett, R. L . , 89, 90, 91(27), 94(27), 97(27),
/00, 572(118), 579 Lasz lo , A . , 447( 186), 449( 186), 473( 186),480 Latour, J. M.,435(130a, 131a),478 L a u , D . Y . K . , 147(68a),233 Laufberger, V . . 64, 69(378),82 Laurel l , C. B . , 64(371), 69(371),82 Lavellee, D. K . , 354(26a), 356(26b, 26d),
364, 468(277), 471(277),483 Lawrence, R. D . , 3 1(39), 72 L a w r i e , C . W . , 147(68),233 L a y , K. L.,420(77),432( 127),434( 127),
Lederer, E . , 33(63), 73 Lee , A . , 572(122),579 Lee , R. Y . , 423(90),477 Leenstra, W. R. , 440( 136), 441( 136),479 Legge , J . W . , 14, 25(16),26, 39, 40( 131), 75,
L i l i e n t h a K H R , 451(194), 453(194), 454(194), 461(194), 480
L i m , C K , 574(138, 139, 140, 142), 576(138, 139, 140, 142), 580
Linder, F . , 297(26),335 L i n d e r , R . E . , 423(98),477 Lines, J . , 321(135),338 Lines , M. T . , 501(58), 535(58), 541(58),551 Linschi tz , H . , 571(1 15), 572(115), 573(115),
Liquori , A M , 56( 163), 76 Little, R. G.,89,100, 447(169), 451(217),
454(217), 468(269), 469(269),479,48/, 482
Ljusberg- Wahren, H . , 468(267), 469(267), 482
Loach, P. A . , 89,100 Lockwood, W . , 298(30), 299(30),335 Loeffler ,R. K . , 565(70),578 Loev. B . , 563(54, 55),578 London, I. M . , 32(52), 41, 42( 175), 44,
46(142),48(I75),7i, 76, 77 Long, J . , 246(35),264 Longo. F. R . , 51(256), 79, 87. 89(34), 92,
McLaughl in , G . , 351(24), 358(24),364 M c L e e s , B. D . , 472(283),483, 568(97), 579 M a c M u n n , C A , 30, 32, 36, 71, 72 Macquet, J. P., 401(35),475 M a h , H . D . , 125(42), 147(42),232 M a k i n e n , M W , 51(265), 79 Makino , R. , 300(40-42),335 Manassen, J . , 473(286),455 Mangoni ,L ,312(84) , JJ6 Mansley, G. E . , 43(229), 50(229), 78 Marchlewski , L . , 38, 39, 40(102), 74 Marchon, J. C, 435 (130a, 13 la), 453( 191).
Mayer, A . , 278(53), 285(53), 288 Mayer , F . , 39, 40(128), 75 Mayer , H . , 309(64),336 Mayo , B C , 375(40), 388 Mehne, L . F . , 468(278),483 Menott i , A. R . , 89,99, 424( 100), 425( 100),
Meyer-Betz , F , 32, 73 Michaelis , L . , 45, 51(147), 64(377), 69(377),
76,82 Mieg, M , 488(17), 491(17), 550 Mieg , W ,321(133),JJS MichI, K H , 266(10),286 Mikhalenko, S A , 383(60a),3£S Mi l l e r C K , 50(219), 78 Mil le r , J. R . , 416(68), 424(68), 425(68),
Mil l ikan , J G , 30( 17), 32(15), 45( 17), 72 Mi l ton , C , 535(47),551 Minnart , K . , 43(239), 50(239), 78 Mironov, A. F . , 169(85),233, 240(17),
Mirsky , A E , 57, 58(323, 324, 344), 59,81 Mispelter, J . , 462(254),482 Mitchel l , J , 488( 13), 490(13), 501( 13),
505(13), 538(13),550 Mitchel l , S W ,70(391),83 Miyauch i , C , 563(44, 45),577 Moitessier, J . , 57, 58(325), 59,81 Momenteau, M . , 450(203a), 454(203a),
455(203a), 262(252, 254, 255),480, 282 Monod , J , 37, 74 Mooney, J. R . , 377(53), 380(53),388,
402(38), 474(38), 476 Moore , S., 42(177, 178), 48(177, 178), 77 M o r a l l e e , K G , 261(250), 282 More l l , D B , 293(14), 299(31, 32), 313(31,
32, W\),334,335,337 Morgan, V. E . , 55(316), 56,81 Morikawa, I., 55(321), 56,81 Morr ison, D. B . . 53, 54, 55(295),80 Morr ison, M . , 42(207), 78, 311,313(92,93,
94),336, 337, 564(63, 64), 578 M o r s i n g h , F . , 224(115), 227(115),234,
273(27),287, 320(130),338 Morton, R. K . , 41, 42(202), 44,76, 77, 78 Morton , T. C . , 566(78),578 Moscowi tz , A . , 423(98),477 Moser, F. H . , 374(27), 379(27),387, 393(14),
475 Moskowi tz , D. W . , 88(15), 99 M o s s , T . H . , 292(10),334, 451(194),
453( 194), 454( 194), 461(194), 480 Moyer , W. W . , 8,26, 326(154, 155),
321(155),338 Miihlbauer, J . , 33(63), 73 Muir , I M H , 32(53), 73 Muirhead, H . , 68(382), 69(382),82 M u l j i a n i , Z , 306(55),336 Muller , A. F . , 369(9, 10),387 Muller , P . M . , 21(26),26 Muller , R. , 294(20), 299(20),335 Miil ler-Eberhard, U , 58(358-360), 60,82 Munck, E . , 423(95), 461(95),477
Nicholas, R. E. H . , 318(117),337, 556(13), 561(22), 567(13), 576, 577
Nicholson, D . C , 284(51),288, 318(112), 322(139),337, 338, 574(139), 576(139), 580
Nicolaus, R. A . , 312(84),336 N i e m , T . , 473(287), 483 Niemierko, W . , 556(16),577 N i s h i d a , G , 291,334 Nishikawa, S., 561(27),561 Nixon , L . , 111(23), 125(23),231 Noble, E. P. , 380(54),388 Norman, G- D . . 19(24),26 Noro, K . , 501(60), 543(60), 544(60),551 Noro, T. , 501(60), 543(60), 544(60),551 North, A . C , 68(382), 69(382),82 Nozaki , M , 55(321), 56,81
Nutter, J . , 562(40),577 Nygaard, A. P. , 50, 77 Nyho lm, R S , 42(201), 77
O
O'Br ien , J. R. P . , 54(297), 55(297),80 O'Br ien , T. P. , 400(30), 427(30), 447(30),
448(30), 449(30), 475 Oester, M. Y . , 410(61), 421(61), 427(61),
Paiade G E , 3 0 , 71 Paleus, S., 54(305), 55(305, 319), 56,80, 81 Palmer, J. M . , 442( 142), 444( 142),479 Palmer, S. E . , 513(35), 514(36), 515(36),551 Palmer, T. F . , 378(49),388 Panayappan, R. , 451(215), 454(215),
462(215), Papaefthymiou, G . C , 451(218), 454(218),
460(218), 481 Pappenheimer, A. W . , Jr., 40( 134), 75 Parish, R . G . , 42(161), 48(161), 76 Park, R. , 505(34),550 Parker, M. J . , 3 10(74), 311 (74),336 Parker, J . , 305(54),336 Parkes, A. S., 29(2), 7/ Parkes, E. A . , 88, 99 P a r n i s , C , 241(20),263
Parrick, J . , 135(58),232 Pabst, A . , 535(47),55/ Pasternack, R. F . , 573(132, 135),579 Pasteur, L . , 70(392),83 Paul, K. G . , 42(157), 46(154), 55(319), 56,
Petering, D. H . , 468(262),482 Peters, R. J . , 53, 54, 55(292),80 Peterson, E . , 44(275), 51 (275), 52(275), 79,
80 Peterson, J. M . , 54(297), 55(297),80 Petryka, Z. J . , 566(76), 568(76), 574(141),
576(141).578, 580 Pettersen, R. C. 486(7, 7a), 487(7), 535(48),
550, 551 Phillips, D . C . , 69(380),82 Phillips, L K ,443(151),479 Piciulo, P , 443( 152), 450(209),454(209),
458(240), 465(209), 466(209),478, 481 Pi lger ,T . B. G . , 43(227), 50(227), 78 Pilgrim, R . L . C , 529(45), 531(45),551 Pillinger, C. T . , 488( 14), 490( 14), 502(25),
Piloty, O . , 32, 46(59), 62(59), 73, 132,232 Pinnock, H. A . , 248(40),264, 468(272),
469(272), 470(2 72), 483 Plane, R. A.,406(44),476, 573(131, 135),579 Piatt, J. R. , 50(197), 51, 77 Plieninger, H . , 105(11),257 Plotz, E . , 327(156),338 ^
P l u s c e c J . , 125(42), 147(42), 232 Pohlmann, H. P. , 488( 15), 491( 15),550 Pollinger, A . , 53, 54(293), 55(293),50 Ponnamperuma, C , 44(275), 51(275),
52(275), 79, 80 Ponomarev, G. V . , 244(29, 32), 262(29),263,
264 Poor, R. W . , 44(247), 51(247), 79, 345(11),
363 Porra ,R . J . , 297(25),335 Porter, C . C . , 58(349),81 Porter, K . R . , 3 0 , 7 / Posnyak, A. L . , 367(8), 369(8),387 Pratt, J. M . , 468(263), 471 (263), 482 Pregl, F . , 58(337), 59,5/ Prentiss, A. M . , 31(34), 72 Preobrazhenskii, N . A . , 169(85),233,
250(44), 256(44), 259(44),264 Prewitt, C. T . , 413(64), 418(64), 427(64),
432(64), 438(64), 444(64), 449(64), 476 Preyer, W . , 55(307), 57, 58(307),80 Price, R . , 104(7). 117(7), 122(7), 123(7),
R e e d , R . 1., 378(49),388 Reichert, E. T . , 55(310), 70(310).80 R e i l , S , 135(55), 232 Remer, H . , 43(245), 50(245), 79 Reuter, F . , 308(59), 336 Reyes, Z . , 451(216), 454(216),481 Rhodes, R. E . . 499(24), 520(24), 521(24),
535(24), 543(24), 544(24), 550 Rianson, W. T . , 89(32), 100 Richards, W. R . , 564(60).578 Richardson, K . , 240(14), 246(14, 38),
Rimmer, J . , 119(32a),231 Rinte lman ,W. L . . 375(36),388 Ripol l , D.,435( 131a),478 Rittenberg, D . , 30, 32(52), 42( 175), 48( 175),
65(12), 71, 73, 77 Roberts, G. C. K . , 47( 166), 48( 166), 66( 166),
67(166), 68(166), 76 Robertson, J. M . , 371( 19), 376( 19), 384(65),
386,387, 388 Robinson, A . B . , 309,336
Robinson, A. R . , 42( 181), 48(181), 77 Robinson, E. A . , 58(352), 60,81 Robinson, G . M . , 132(50),232 Robinson, R. , 132(50),232 Robinson, W T , 450( 199), 454( 199),
455( 199), 456(199),465(199), 466( 199), 480
Rocha-Gonsalves, A . M. cTA., 161(81), 170(81), 179(92),233, 265(6), 278(54, 55), 281(6), 285(53-55),286, 288
Roche, M . , 244(26), 262(26),263, 321(136), 338
Rochester, C. H . , 345(12),363, 367(7), 368(7), 387
Roder, A . , 451(220, 221, 222), 454(220, 221, 222).481
Sakakibura ,S. , 309(69),336 Sales, K. D . , 450(208), 454(208),481 Sa lmond ,W. S., 21(26),26 Sams, J. R . , 423(95), 450(188a),453(188a),
454( 188a), 459(188a), 461(95),477, 480 Samuels, E . , 105(10),231 Sancovich, H . A . , 280(32a),287 San i t zke ,G . , 349(18a),364 Sano, S., 9(9),26, 244(27),263, 308(57),
309(57, 67-69), 321(132),336, 338 Sarancheck, H. J . , 61, 62(365),82 Sasada, Y . , 346(14a), 363(35),363, 364,
Saunders. R. A . , 378(49),388 Sayer, P . . 432( 128b), 437( 128b),47£ Schaefer, H . . 129(48).232 Schaffer, A . M . , 378(52),388 Scha tz ,G ,69 ,&? S c h e e r , H . , 25(32),27, 423(88), 427(73),
439(88), 474(73), 477 Scheidt, W. R . , 393( 15), 395( 15), 397(15),
Schejter, R . , 40(11 la), 44(11 la), 50( 111a), 5 1 ( l l l a ) , 6 7 ( l l l a ) , 7 4
Schenkman, J. B . , 43(245), 50(245), 79 Scherer ,M ,98, / t f t f Schmid, R. , 32(42), 36(42), 42, 46(85), 72, 74 Schmidt, C. F . , 30( 14), 34(14), 72 Schmidt, R . , 108(22),231 Schneehage, H. H . , 44(255), 51(255), 79,
Schwartz, V . , 556(11),576 Schwarz, F. P . , 306(55),336, 422( 125),47#,
432(125), 433(125),478 Schultz, J H , 32, 72 Scott, A. I., 135(56),232 Scott, C. R . , 562(40),577 Scott, J. J . , 343(9), 344(9), 345(9), 363(9),
363 Scott, R . G . , 25(32),27 Seamans, L . , 423(98), 477 Seba ld ,W. , 69(383),82 S e e l y , G . R. , 324( 149),324, 392(6),474 Seeman,C. V . , 305(5\),335 Sei tz ,G. ,49( 187a), 77 Sekuzu,I. ,315(104),3J7 Senebier, 38(40, 103), 74 Setsune, J. I., 447(178), 449( 178), 468( 178).
469(178), 470(178),480 Seyffert, R . , 43(223), 50(223), 78, 311(77,
338 Shore, V C , 69(380),82 Shulga, A. M . , 367(8), 369(8),387 Shulman, R. G . , 278(54), 285(53, 54),288 Shutt leworth,R. , 105(10), 2 J / S idd iqu i ,Z V , 440(145),479 Sidwell , A. F . , 44(267), 51(267), 79 S i e b e r , N . , 55(308),<S0 Siedel, W . , 14,26, 87,95,97,99, 149(70),
233 Siegelman, H. W . , 19(23),26 Sievers, G . , 293, 295(13),334, 562(39),577 Simmonds, D. H . , 42(214), 64(372), 69(372),
78, 82 Simon, S R , 47( 165, 166), 48( 166), 66( 165,
166), 67(165, 166), 68(166), 76 Simone i t ,B . R. , 538(51),551 Singer, R. B . , 30( 14), 34(14), 72 Singer, S.J. ,30(18), 72 Singh, R . , 347(17), 363 Sinyakov, G. N . , 367(8), 369(8), 387 Skapski, A . C , 444(155),479 Skeggs, L . , 54, 55(296),80 Sklar, L . , 92(38), 94(38), 98(38), 100 Slade, E. F . , 47( 167), 66(167), 76 Slama, J. T . , 309,336 Slater, E . C , 43(217), 78 Slater, G . , 573(130),579 Sligar, S . G . , 416(72), 476 Smith, D. B . , 40(137), 75 Smith, D . W . , 457(236), Smith, E. L . , 40, 43, 50( 11 la), 51(111),
67(111), 74, 75 Smith, G. D . , 522(43), 538(52),551 Smith, H . W . . 309(65),336 Smith, K. ,427( 103a),477 Smith, K. M . , 107(13), 119(32a), 127(44a),
Stevens, T. S., 105(10),2J/ Stewart, M . , 298(32), 299(32), 313(32, 96),
335,337 Stich, W . , 559(23), 560(23),577 Stimson,C ,356(26c) , i64 S t i t t ,F . , 49(183), 77 Stojanac, N . , 125(42), 147(42),232 Stokes, G . G . , 70(390), 82 Stokvis, B. J. E . , 36(83, 84), 73, 74 Stoll , A . , 32(61), 39, 7 i , 324(146, 150).
Stoll , M S , 574(138, 139, 140, 142) 576(138, 139, 140, 142), 580
Stone, A . , 363(36),364 Stoppa, H . , 419(22), 422(22),475 Storm, C. B . , 535(49),55] Stotz, E . . 42(207), 77, 311(81), 313(92, 93,
94),336,337, 564(63, 64), 578 Strain, H . H . . 25(31),27 Strandberg, B. E . , 67(380), 69(380),82 Strangeways, D. H . , 54(297), 55(297),50 Straub, D. K . , 440(171), 447(171), 449( 171),
Streibl, M . , 542(59),551 S t r e l l , M , 8 , 2 6 Strittmatter, R . , 43, 50(240, 241), 78 Strosher, M . , 501(32), 503(32), 520(32),
522(32), 550 Studier, M. H . , 25(31, 32),27 Stults. B. R. , 442(144),479 Stynes, D. V . , 468(261, 273, 274), 469(273,
274), 470(273, 274),482, 483 Stynes, H . C . , 468(261),452 Subba Rao, B . C . , 268(18), 287 Suckling, C. J . , 278(41a), 281(40, 41a),288,
323(144), 338 Sugimoto, N . , 454(223), 457(223),481 Sullivan, J. F . , 400(32), 401(32), 402(32),475 Summerville, D. A . , 463(258a),452 Supphayen, D . M . , 280(32b),287 Surgenor, D. M . , 58(362), 60,52 Suslick, K. S., 457(232, 232a),481 Suzuki , K . , 409(50), 435( 130), 440(50),
441(135),476, 478 , 569(101),579 S v e c , W . A . , 25(31, 32),27 Sweeney. A . , 342(4), 346(4), 347(4, 18),
480 Takenaka, A . , 363(35),364, 399(29), 468(29),
469(29), 475 Tanford, C . , 42( 160), 46( 160), 48(160), 76 Tang, S. C, 451(218, 224), 454(218, 224),
460(218, 224),481 Tarlton, E. J. 169(87), 224(87), 225(87),233,
265(3), 273(3),286, 319(120),337 Tasset, E . L . , 442(144),479 TaubeR. , 377(48),388 Taylor, D. N . , 313(100), 315(100),337 Taylor, G. A . , 392(13), 393(13), 409(13),
425( 13), 440(13), 442(13), 446(13), 475
Taylor, J. F . , 58(335), 58 Taylor, K. T . , 378(50), 379(50),388 Tcherniac, J.,374(32),388 Teichmann, L . , 31, 72 Terrell , R. J . , 345(12),363, 367(7), 368(7),
387 Terry, W . G . . 134(53),232 Theophanides,T. , 401(35),475 Theorell , H . , 30, 42(155, 157), 43(236),
Thorne, E. J . , 87, 95(6), 96(6), 97(6), 99 Thorp, R . , 447( 166), 448( 166), 449( 166), 479 Thorpe, A . , 451(215), 454(215), 462(215),
481 Thudichum, J. L. W . , 35, 75, 297(24),335 Timkovich , R , 420( 104), 425( 104), 426( 104),
477 Tooth, B. E . , 32(49), 73 T o n n , B . , 422(111), 423(111), 478 T o n n , M . , 451(214), 454(214), 461(214), Torrens, M. A . , 459(246), 461 (246),482 T o s s i , L , 42(213), 78 T o w i l l , R . , 574(137, 142), 575(137), 576(142),
580 Townsend, C. A . , 135(55),232 Traylor, T. G . , 327(160, 161),339, 450(203),
Trochagrimshaw, J . , 346( 14b),363 Tschamber, T . , 356(23, 27), 357(27),364 Tschirch, A . , 38, 39, 40(101), 74 T s i n , T . B . , 423(95), 450( 188a), 453( 188a),
Tsvirko, M ,89,100 Tswett, M . , 39, 40(122), 70(388), 75, 82 T u e y , G . A. P . , 384(65, 66), 386(65, 66),388 Tulinsky, A . , 43(257), 251(257), 79,
420(104), 425(104), 426(104), 477 Turner, D. R . , 457(238),482 Tynan, E . C , 533(46), 534(46),557
U
Unsworth, J . F . , 127(44a),232 U r a t a , G . , 37(95), 74 U l l m a n , E F , 89(31), 100
V
Valasinas, A . , 125(41), 126(41),232, 316(108), 337
Valenta, Z . , 8(7b),26, 236(6), 238(6),263, 281(34), 287
Vallee, B. L . , 431(120), 432(120),478 van de Broek, P. , 246(35), 248(41),264 van K a a m , J . , 404(40), 407(40), 423(40),
Vannotti , A , 3 9 , 40(127), 75 Van Slyke, D D , 39, 40(123), 75 Varadi , V . , 95(42), 100 569(104), 572(104)
579 Vaska , L . , 454(225), Vaughan, G. B . , 533(46), 534(46),551
Velapoldi , R. A . , 424(135), 435(130), 441(135),478, 569(101),579
Vel ick , S. F . , 43(240), 50(240), 78 Venerable, D . , 447( 166), 448( 166), 449( 166),
479 Venteicher, R. F . , 421(117), 429( 117),
430(117),431(114, 120),432(117, 120), 478
V e n t u r e G . C . , 573(132), 579 Verdei l , 40(133), 75 Vernon, L . P . , 392(6),409(6),474 Vestling, C S , 58(335, 349), 60 ,5 / Vierordt, K . , 38,40(118, 119), 75 V i o h l , P , 156(80) 160(80), 169(80),
204(101), 233,234 Viscont ini , M . , 112(25),231 Viswanatha, V . , 346( 14b), 363 Vlaes, F , 49, 77 Vohwinkel , F . , 409(50), 440(50), 441(135),
476,478, 569(101),579 Voigt, H . , 88(13), 99, 302(44), 333(44),335,
447(184), 449(184), 480 Voldodarskaya, G. Y . , 252(48), 256(48),264 V o l ' K e n s h t e i n , M V , 486(3), 507(3),
539(3), 550 V o l k e r , W . , 313(97),337 Vollmann, H . , 374(29), 375(29), 337(29),
379(29), 387 V o l z , H . , 8(7b),26, 236(6), 238(6),263,
281(34), 287 von d e r H a a r , F . , 502(27), 550 von der Weid , E . , 374(33),388 von Kol l ike r , A , 38, 40( 114), 75 von Kruger, F . , 58(336, 343), 59,81 von Maltzan, 90(37),/tftf von M i s e s , R , 525(44), 551 von Nenck i , M . , 55(303, 308),80 von Rebay, A . , 384(62, 63),388 von Seemann, C, 55(313), 56(313),
244(28), 263 von Zeynek, R., 58(341), 59,81 Vouschne, H. G . , 349( 18a),364
W
Wagner, G. C . , 450(202), 454(202), 455(202), 458(202), 480
Wicholas, M . , 450(21 la), 454(21 la),481 Wickliff , J L 327(I58) ,JJ9 Wickwar , H . , 345(12),363, 367(7), 368(7),
387 Wiedemann, H . , 556( 14), 565( 14),577 Wightman, R. H . , 329(169),339 Wilchek. M . , 564(66),578 Wilkerson, C. J . , 450(201), 454(201).
455(201), 280 Wilkinson, G . , 416(18), 418(18). 439(18).
458(18), 473(18),475 Will iams. A. E . , 378(49), Will iams, G E , 572( 127), 579 Will iams, K. W . , 563(51), 577 Williams, N. R . , 115(30), 125(30), 126(30),
127(30), 174(88),231,233, 265(2),286 Will iams, R. G . , 43(215), 78 Will iams, R J P , 42, 49( 185), 50, 51, 77,
451(220, 222), 454(220, 222). 457(236). 481
W i l l s o n . C . D . , 134(54),232, 267(13),286
Wills ta t ter ,R. , 14,26, 32,33,38,39,40(61), 53, 54, 55(293, 309), 73, 80, 321(133), 324(146, 150), 325(151), 326, 392(5), 393(5), 409(5), 450(5), 453(5), 474, 488(17),491(17),550
Wilson, C . G . , 309(65),336 W i n a n s , C . F . , 108(21),231 Winkelman, J. ,573(130, 133), 579 Winkler , F . , 87, 95, 97,99, 149(70),233 Winter, M . , 354(26, 355(26), 360(26),364 W i s e , C . D . , 58(353), 60,81 W i t h , T . K . , 14, 18,26, 32(51), 7J, 560(26),
561(22), 562(42, 43), 564(59), 566(43), 577, 578
Wittmann-Liebold, B . , 30(21), 67(21), 72 Wolberg, A . , 473(286),483 W o n g , C . P. , 421(116, 117), 422(116),
478 Wong, J . , 440( 139), 441 (139),479 Wong, K. L. ,450( 188a), 453( 188a),
454( 188a), 459( 188a), 480 Woodrow, G . N . , 563(47a),577 Woodward, I., 371 (19), 376( 19), 387 Woodward, R. B . , 8 , 2 6 , 177, 195(74),233,
236(6), 238(6),263, 281(6),287, 539(54), 55 L 558(18), 577
Wootton, I. D. P. . 54, 55(297),80 Wright, J . M . , 380(54),388 Wyman, J . , Jr., 39, 40( 109), 41, 47, 49(184),
66,74, 77
Y
Yagodina, L. A . , 383(60a), J&S Yamamoto, A. ,443( 151),479 Yamamoto, H . , 563(47a),577 Yamanashi, B. S., 43(258), 51(258), 55(321),
56,79,81 Yamane, T. , 278(54), 285(53, 54),288 Yamazaki , I., 300(40-42),335 Y a u , J . C . N . , 439(134),478 Yee, S., 442(141), 443(141),479 Y e n , T. F . , 499(24), 520(24), 521(24),
Aroyldipyrrylmethanes, 90 Atropisomers, 89 Azafulvenium ions, in porphyrin synthesis,
93
electrophilic attack, 271 nomenclature, 14 oxidation to bilenes-/?, 255 5-oxo,255 Bilatrienes, nomenclature, 14 Bilatrienes-abc from biladienes-abc, 246 Bilenes, nomenclature, 14 Bilenes-a, from bilenes b, 244, 253 Bilenes-b
from bilanes, 255 copper promoted cyclization, 252 cyclization to porphyrins, 249-257 1,19-dicarboxylate esters, cyclization with orthoformate, 257 cyclization to porphyrins, specific examples, 260 l,19-dimethyl,256 from 1,19-dimethylbiladienes-rtc, 258 from dipyrrylmethanes, 249 electronic spectra, 273 l-formyl-19-methyl,256 from 5-formyldipyrrylmethanes,
250 1-methyl, 256 properties, 249 rearrangement to bilenes-a, 249,
to azaporphyrins, 249 from 5-bromo-5'-bromomethylpyr- romethenes, 242 conversion to monoazaporphyrins, 366 copper promoted cyclications, 238 cyclization to porphyrins, 238-249 to 1-methyltetradehydrocorrins, 246 from 5-methyl-5-unsubstituted
pyrromethanes, 242 properties, 244 synthesis, 238, 242 Bilanes from bilenes-b , 255 dehydrogenation to bilenes-, 255 electronic spectra, 273
1-Bromo-19-methylbiladienes, cyclization to porphyrins, specific examples and experimental details, 261 Bromoporphyrins, hydrogenolysis, 282 t-Butyl hypochlorite methylpyrrole chlorination, 148, 150, 159 oxidation of bilanes to bilenes-6, 255 oxidation of methylpyrrylketones, 269 t-Butyl pyrrole carboxylates, removal of t-butyl group, 153
from acetoxymethylpyrroles, 169 from azafulvenium cations, 167 from bromomethylpyrroles, 169 from formaldehyde, 166 from lithium pyrrole carboxylates, 174
unsymmetric, 167
Vilsmeier-Haack formylation, 182 Dipyrrylthioketones, see Pyrrylthioketones Dry column chromatography of porphyrins, 563 Dyestuffs, phthalocyanines, 379
isomer separation by column chroma- tography, 564 isomer separation by tic, 562
2-Formyl-4-vinyl-deuteroporphyrin, see
Spirographis porphyrin a-Free pyrroles
conversion to pyrromethenes, 199, 204 reaction with acetoxymethylpyrroles, 169 reaction with bromomethylpyrroles, 169 synthesis, 162
occurrence
petroleum and bitumens, 517 sediments, 511 shales, 533 petroporphyrins distribution, 520 mass spectra, 519 structural characterization
number of isomeric porphyrins, 531 number of petroporphyrins, 528 oxidation and mass spectra, 525 oxidation to maleimides, 521 properties, 511 vanadyl porphyrins, 513, 517 Germanium porphyrins, 436 Glaucobilin, nomenclature, 18 Glyoxylic acid, reductive alkylation of pyr- roles, 124 Gold porphyrins, 471 redox chemistry, 473 synthesis, 449 Griffith model of oxygenation, 456
G
Gallium porphyrins, v-oxo dimers, 429 Gas chromatography of geoporphyrins, 488
of porphyrins, 569 Gatterman formylation, 146 Geeldikkop, 32 Gel filtration of porphyrins, 564 Geochemistry of porphyrins, 51 Geological time scale, 549 Geoporphyrins
Iodopyrroles deiodination, 163 synthesis, 162 Ionic radius effect on oxidation states of metallopor- phyrins, 411 of metal, effect on porphyrin metallation, 411
Iridium porphyrins, synthesis, 449 Iron sorption, 64
in heme and heme proteins, 55 insertion into hematoporphyrin, 298 migration in body, 63 removal from hemin, 291 raeso-tetraphenylporphyrin-M-oxo dimer
X-ray structure, 400 transfer into cells, 64
Iron octaethylporphyrin fluoride, electronic spectrum, 414
Iron octaethylporphyrin /u-oxo dimer, electronic spectrum, 414 Iron porphyrins, see also Hemes, Hemo- chromes, Hemins, Hematins, Hemi- chrome salts and specific compounds
Mesoporphyrin II dimethyl ester, synthesis, 226 Mesoporphyrin III dimethyl ester, synthe-
sis, 240 Mesoporphyrin XI, synthesis, 275, 278 Mesoporphyrin XI dimethyl ester, synthe- sis, 257 Mesoporphyrin XIII dimethyl ester, synthe-
sis, 228 Mesotetraphenylporphyrin see also Metaloporphyrins chromatography, 571 synthesis, 89 Metal alkoxides, for porphyrin metallation, 49 Metal alkyl
cobalt porphyrins, 470 iron porphyrins, 470
for porphyrin metallations, 408 Metal carbonates, see Porphyrin chromatog- raphy, 567 Metal carbonyls, for porphyrin metallation,
2- Methyl-3-oxobutyraldehyde, 105 5-Methyl-5'-unsubstituted pyrromethenes, conversion to biladienes-^c, 242 l-Methylbiladienes-ac, cyclization to por phyrins,- specific examples and experi- mental details, 258 I-Methylbilenes-/? copper promoted cyclization to porphy- rins, 256 cyclization to porphyrins, specific exam- ples and experimental details, 259 N-Methylchlorins
esters, chromatography, 565 esterification, 576 vV-ethoxycarbonyl, 350 X-ray structure, 345 a and b faces, nomenclature, 22 Fischer synthesis, 209 b-formylation, 282 from azafulvenium ions, 93 from biladienes-flc, 248, 258, 261 from bilenes-6, 249, 259, 260 from chlorophylls, 324-329 from 5,5'-diformylpyrrylketones and
Platinum meso-tetra(p-toly l)porphyrin, dipyrrylmethanes, 221 from 1,19-dimethylbilenes-b and copper, electronic spectrum, 415
Platinum porphyrins, 471 256 from dipyrrylmethanes, 175, 209 redox chemistry, 472 from l-formyl-19-methylbilenes-6, 256 synthesis, 449
Polyamide column chromatography of metalloporphyrins, 564
from Mannich bases, 87 from meconium, 322
from 1-methylbilenes-b and copper, 256 tic of metalloporphyrins, 563 Polymers, silicon phthalocyanines, 402 Polypyrromethenes, intermediates in por- phyrin synthesis, 95 Porphin
from monopyrroles, 85-100 from a-oxobilanes, 269, 275 from b-oxobilanes, 274, 278 from porphodimethenes, 98 from porphomethenes, 98 nomenclature, 4 from porphyrinogens, 91 synthesis, 85
Porphinato, nomenclature, 23 Porphobilinogen
from pyrroles, 85-100 from pyrromethenes, 211
and copper, 239 gas chromatography, 569 gel filtration, 564 geochemistry, 51, 485-551 halogenated, 89
from 6-azaindoles, 135 lactam, synthesis, 135
Porphodimethene(s) intermediates in porphyrin synthesis, 98
nomenclature, 13
HCl-number, 585 conversion to coporporphyrin III, 329 isotopically labelled, 244, 248 nomenclature, 7
heats of sublimination, 587 isotopically labeled, 244, 248, 284 MacDonald synthesis, 177 oxidation to diformyldeuteroporphyrin,
302 metabolism, regulation, 37 metal insertion, see metalloporphyrins reduction, 299