6562
J. Org. Chem. 1993,58, 5562-5570
Recent Reviews. 31 compiled by Samuel H. Wilen Department of Chemistry, The City College, City University of New York,New York,New York 10031
Reviews are listed in order of appearance in the sources indicated. In multidisciplinary review journals, only those reviews which fall within the scope of this Journal are included. Sources are listed alphabetically in three categories: regularly issued review journals and series volumes, contributed volumes, and other monographs. Titles are numbered serially, and these numbers are used for reference in the index. Major English-language sources of critical reviews are covered. Encyclopedic treatises, annual surveys such as Specialist Periodical Reports, and compilations of symposia proceedings are omitted. This installment of Recent Reviews covers principally the early part of the 1993 literature. Previous installment: J . Org. Chem. 1993,58(14), 3775-3782. For regularly issued journals and series volumes, the coverage in this installment continues from the last item included in Recent Reviews 30.
Regularly Issued Journals and Series Volumes Accounts of Chemical Research 1. Ikekawa, Nobuo; Morisaki, Masuo; Fujimoto, Yoshinori. Sterol metabolism in insects: dealkylation of phytosterol to cholesterol. 1993, 26(4), 139-46. 2. Hansch, Corwin. Quantitative structure-activity relationships and the unnamed science. 1993,26(4), 147-
14. Pfaltz, Andreas. Chiral semicorrins and related nitrogen heterocycles as ligands in asymmetric catalysis. 1993,26(6), 339-45. 15. Iwamura, Hiizu; Koga, Noboru. Studies of organic
di-,.oligo-, and polyradicalsby means of their bulk magnetic properties. 1993, 26(6), 346-51.
53. 3. Gubnard, Daniel; Gubritte-Voegelein, Francoise;
Acta Chemica Scandinavica
Potier, Pierre. Tax01and taxotere: discovery, chemistry, and structure-activity relationships. 1993,26(4), 160-7. 4. Look, Gary C.; Fotsch, Christopher H.; Wong, Chi Huey. Enzyme-catalyzed organic synthesis: practical routes to aza sugars and their analogs for use as glycoprocessing inhibitors. 1993,26(4), 182-90. 5. Menger, Fredric M. Enzyme reactivity from an organic perspective. 1993,26(4), 206-212. 6. Weisshaar, James C. Bare transition metal atoms in the gas phase: reactions of M, M+, and M2+ with hydrocarbons. 1993,26(4), 213-19. 7. Collum, David B. Solution structures of lithium dialkylamides and relatedN-lithiated species: results from BLi-lSN double labeling experiments. 1993,26(5), 227-
16. Diederich, Francois; Smithud, David B.; Sanford, Elizabeth M.; Wyman, Tara B.; Ferguson, Stephen B.; Carcanague, Daniel R.; Chao, Ito; Houk, K. N. Solvent effects in molecular recognition. 1992,46(3), 205-15. 17. Famulok, Michale; Nowick, James, S.; Rebek, Jr., Julius. Self-replicating systems. 1992, 46(4), 315-124. 18. Bickelhaupt, Friedrich. The importance of (intramolecular) solvation in organomagnesium chemistry.
34. 8. Lengyel, Istvh; Epstein, Irving R. Turing structures in simple chemical reactions. 1993,26(5), 235-40. 9. Grushin, Vladimir V. Reductive elimination of
hydrogen chloride from chloro hydrido transition metal complexes: an efficient and simple method for generation of electron-rich, coordinatively unsaturated, reactive intermediates. 1993, 26(5), 279-86. 10. Wayner, Danial D. M.; Parker, Vernon D. Bond energies in solution from electrode potentials and thermochemical cycles. A simplified and general approach. 1993,26(5), 287-94. 11. McAdoo, David J.; Morton, Thomas Hellman. Gasphase analogs of cage effects. 1993,26(6), 295-302. 12. Gleiter, Rolf; Kratz, Detlef. “Super” phanes. 1993, 26(6), 311-18. 13. Fife, Thomas H. Kinetic and mechanistic effects
of ease of C-N bond breaking in amide hydrolysis. The mechanisms of hydrolysis of N-acylimidazoles and Nacylbenzimidazoles. 1993,26(6), 325-31.
1992,46(5), 409-17. 19. Hoz, Shmaryhau. The anti-traditional interpretation of the LFER mechanistic message. 1992, 46(6), 503-507. 20. Chanon, Michel. The variety of molecular schemes
a t the border between polar and electron-transfer (ET) mechanisms. 1992,46(8), 695-706. 21. Guerriero, Paolo; Vigato, Pietro Alessandro; Fenton, David E.; Hellier, Paul C. Synthesis and application of macrocyclic and macroacyclic Schiff bases. 1992,46(11), 1025-46. 22. Wozniak, Marian; van der Plas, Henk C. Amination of nitroazaaromatics. 1993, 47(2), 95-101. 23. Undheim, Kjell; Benneche, Tore. Metalation and
metal-assisted bond formation in ?r-electron deficient heterocycles. 1993, 47(2), 102-21. 24. Martin, Arnold R.; Yang, Youhua. Palladiumcatalyzed cross-couplingreactions of organoboronic acids with organic electrophiles. 1993, 47(3), 221-30. 26. Funicello, Maria; Spagnolo, Piero; Zanirato, Paolo. Intramolecular cyclizations and ring-cleavage reactions of five-membered heteroarylnitrenes and their precursors. 1993, 47(3), 231-43. 26. Dehaen, Wim; Becher, Jan. Ring-opening of fivemembered heteroaromatic azides and nitrenes. 1993, 47(3), 244-54.
0022-3263/93/1958-5562$04.00/00 1993 American Chemical Society
J. Org. Chem., Vol. 58, No.20, 1993 5563
Recent Reviews 27. Fringuelli, Francesco; Minuti, Lucio; Pizzo, Ferdinando; Taticchi, Aldo. Reactivity and selectivity in Lewis acid-catalyzed Diels-Alder reactions of 2-cyclohexenones. 1993, 47(3), 255-63. 28. Annby, Ulf; Karlsson, Susanne; Gronowitz, Salo; Hallberg, Anders; AlvhU, Joergen; Svenson, Rolf. Hydrozirconation-isomerization. Reactions of terminally functionalized olefins with zirconocene hydrides and general aspects. 1993,47(5), 425-33. Advances in Photochemistry 29. Ramamurthy, V.; Weiss, Richard G.; Hammond, George S. A model for the influence of organized media on photochemical reactions. 1993, 18, 67. 30. Braun, Andre M.; Jakob, Laurent; Oliveros,Esther; Oller do Nascimento, Claudio A. Up-scaling photochemical reactions. 1993, 18, 235. 31. Neckers, Douglas C.; Valdes-Aguilera, Oscar M. Photochemistry of the xanthine dyes. 1993, 18, 315. Angewandte Chemie, International Edition in English 32. Kunz, Horst; Ruck, Karola. Carbohydrates as chiral auxiliaries in stereoselective synthesis. 1993,32(3), 33658. 33. Kessler, Horst. Peptoids-a new approach to the development of key pharmaceuticals. 1993,32(4), 543-4. 34. Muller, H a n s - M a r t i n ; Seebach, Dieter. Poly(hydroxybutanoates): A fifth class of physiologically important organic biopolymers. 1993,32(4), 477-502. 35. Reiser, Oliver. Palladium-catalyzed, enantioselective allylic substitution. 1993, 32(4), 547-49. 36. Kaupp, Gerd; Haak, Michael. Absolute asymmetric synthesis by irradiation of chiral crystals. 1993, 32(5), 694-95. Chemical Reviews 37. Lissi, E. A.; Encinas, M. V.; Lemp, E.; Rubio, M. A. Singlet oxygen O#$) bimolecular processes. Solvent and compartmentalization effects. 1993,93(2), 699-723. 38. Winterfeldt, Ekkehard. Enantiomerically pure cyclopentadienes. 1993, 93(2), 827-43. 39. Parkin, Gerard. Bond-stretch isomerism in transition metal complexes: a reevaluation of crystallographic data. 1993, 93(3), 887-911. 40. Heinekey, D. M.; Oldham, Warren J. Jr. Coordination chemistry of dihydrogen. 1993, 93(3), 913-26. 41. Strauss, Steven H. The search for larger and more weakly coordinating anions. 1993,93(3), 927-42. 42. Sutton, Derek. Organometallic diazo compounds. 1993,93(3), 995-1022. 43. Hanusa, Timothy P. Ligand influences on structure and reactivity in organoalkaline earth chemistry. 1993, 93(3), 1023-36. 44. Saxena, Ani1 K.; Hosmane, Narayan S. Recent advances in the chemistry of carborane metal complexes incorporating d- and f-block elemenb. 1993,93(3), 1081124. 45. Fehlhammer, Wolf P.; Fritz, Marcus. Emergence of a CNH and cyano complex based organometallic chemistry. 1993, 93(3), 1243-80. 46. Hoveyda, Amir H.; Evans, David A.; Fu, Gregory C. Substrate-directable chemical reactions. 1993,93(4), 1307-70. 47. Chuit, Claude; Corriu, Robert J. P.; Reye, Catherine; Young, J. Colin. Reactivity of penta- and hexacoordinate
siliconcompounds and their role as reaction intermediates. 1993, 93(4), 1371-448. 48. Otera, Junzo. Transesterification. 1993, 93(4), 1449-70. 49. Toshima, Kazunobu; Tatsuta, Kuniaki. Recent progress in O-glycosylation methods and its application to natural products synthesis. 1993,93(4), 1503-31. 50. Collins, Paul W.; Djuric, Stevan W. Synthesis of therapeutically useful prostaglandin and prostacyclin analogs. 1993,93(4), 1533-64. 51. Sander, Wolfram; Bucher, Goetz; Wierlacher, Stefan. Carbenes in matrixes: spectroscopy, structure, and reactivity. 1993, 93(4), 1583-621. 52. Baudler, Marianne; Glinka, Klaus. Contributions to the chemistry of phosphorus. 218. Monocyclic and polycyclic phosphines. 1993, 93(4), 1623-67. Heterocycles 53. Yanada, Reiko; Harayama, Takashi; Yoneda, Fumio. Chemistry on the damage and repair of thymine and thymidine derivatives. 1993, 35(1),461-81. 54. Katritzky, Alan R.; Gordeev, Mikhail F. Heterocyclic rearrangements of benzofuroxans and related compounds. 1993,35(1), 483-518. 55. Haider, Norbert; Heinisch, Gottfried. Recent advances in the chemistry of condensed pyridazines: synthesis of bi- and tricyclic systems by annelation of five-, six-, and seven-memberedrings to a preformed 1,2-diazine nucleus. 1993, 35(1),519-38. 56. Meth-Cohn, Otto. The synthesis of pyridines, quinolines and other related systems by the Vilsmeier and the reverse Vilsmeier method. 1993,35(1), 539-57. 57. Martin, Michael J.; Dorn, Linda J.; Cook, James M. Novel pyridodiindoles, azadiindoles, and indolopyridoimidazoles via the Fischer-indole cyclization. 1993, 36(l), 157-89. 58. Li, Wen-Ren; Han, So-Yeop; Joullib, Madeleine M. The detoxin complex-a naturally occurring safener. 1993, 36(2), 359-88. 59. Chimirri, Alba; Gitto, Rosaria; Grasso, Silvana; Monforte, Anna Maria; Romeo, Giovanni; Zappala, Maria. Annulated 1,5-benzodiazepines. Part I. Three, four, and five membered rings. 1993, 36(3),601-37. 60. Chimirri, Alba; Gitto, Rosaria; Grasso, Silvana; Monforte, Anna Maria; Romeo, Giovanni; Zappala, Maria. Annulated l,&benzodiazepines. Part 11. Six membered rings. 1993, 36(4), 865-90. Journal of Heterocyclic Chemistry 61. Pfleiderer, Wolfgang. Pteridines. Properties, reactivities, and biological significance. 1992, 29(3), 583605. 62. Pattenden, Gerald. Synthetic studies with natural oxazoles and thiazoles. 1992,29(3), 607-18. 63. Isobe, Minoru; Nishikawa, Toshio; Yamamoto, Noboru; Tskiyama, Takahiro; Ino, Akira; Okita, Takaaki. Methodologies for synthesis of heterocyclic compounds. 1992,29(3), 619-24. 64. Shinkai, Ichiro. A practical asymmetric synthesis of a novel topically active carbonic anhydrase inhibitor. 1992,29(3), 627-30. 65. Winterfeldt, Ekkehard. Directed stereoselectivity in alkaloid synthesis. 1992,29(3), 631-38. 66. Rees, Charles W. Polysulfur-nitrogen heterocyclic chemistry. 1992, 29(3), 639-51.
5564 J. Org. Chem., Vol. 58,No. 20,1993 67. Speckamp, W. N. New aspects of old reactions. Cations and radicals in heterocyclicsynthesis. 1992,29(3), 653-74. 68. Catsoulacos, P.; Catsoulacos, D. On the synthesis of pyrido[3,2,1-kllphenothiazine, quino[8,1-bc1[1,41benzothiazepine and their derivatives. 1992,29(4),67582. Natural Product Reports 69. Ward, R. 5. Lignans, neolignans, and related compounds. 1993,10(1), 1-28. 70. Led$,J. R. Muscarine, oxazole, imidazole, thiazole, and peptide alkaloids and other miscellaneous alkaloids. 1993,IO(1) 29-60. 71. Midtad, J, P. Indolizidine and quinolizidine alkaloids. b93,10(1),51-70. 72. Dickinson, J. M. Microbial pyran-2-ones and dihydropyran-Bones. 1993,10(1), 71-98. 73. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids. 1993,10(2), 99-108. 74. Ley, S.V.; Denholm,A. A,; Wood, A. The chemistry of azadirachtin. 1993,10(2), 109-57. 75. Hanson, J. R. Diterpenoids. 1993,10(2), 159-74. 76. Fodor, G.; Dharanipragada, R. Tropane alkaloids. 1993,10(2), 199-206. New Journal of Chemistry 77. Eberson, Lennart. Outer-sphere electron transfer reactions, rare events in organic chemistry? 1992,16(12), 151-6. 78. Meunier, Bernard. Potassiummonopersulfate just another primary oxidant or a highly versatile oxygen atom donor in metalloporphyrin-mediated oxygenation and oxidation reactions. 1992,16(1-21, 203-11. 79. Shilov, A. E. Dinitrogen fixation in solution in the presence oE iron complexes. Intermediates and mechanism. 199% 16(1-!& 213-18. 80. Dietrich, Bwhecker C.; Satwage, J. P. Synthetic molecular bote. 16(1-2), 277-85. 81. Astruc, Didier. Transition metal sandwiches as reservoirs of electrons, protons, hydrogen atoms and hydrides: molecular activation and electronics. 1992, 16(1-2), 305-28. 82. Bador, Pascal; Surrel, Marie Noelle. Computer systems for searching of chemical reaction databases and systems for computer-aided design of organic synthesis. 1992,16(3),413-23. 83. Ephritikhine, Michel. Recent advances in organoactinide chemistry. 1992,16(4),451-69. 84. Harcourt, Richard D. Valence bond structures and organic chemistry. 1992, 16(6), 667-70. Progress in the Chemistry of Organic Natural Products 85. Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. The taxane alkaloids. 1993,61,1-192.
Pure and Applied Chemistry 86. Deslongchamge, Pierre. Transannular Diels-Alder reaction on rnamxycles. A general strategy for the synthesis of poIycyGlic compounds. 1992,64(12), 183147. 87. Hayashi, Temio; Uozumi, Yasuhiro. Catalytic asymmetric synthesis of optically active alcohols via hydrosilylation of olefins with a chiral monophosphinepalladium catalyst. 1992,64(12), 1911-16.
Recent Reviewe 88. Hafner, Klaus; Lindner, Hans Joerg; Luo, Weimei; Meinhardt, Klaus Peter; Zink, Thomas. Novel pericyclic reactions in a-perimeter chemistry. 1993,65(1), 17-25. 89. Hart, Harold. Iptycenes, cuppedophanes and cappedophanes. 1993,65(1), 27-34. 90. Hopf, Henning; Witulski, Bernhard. Cyanoalkynes: magic wands for the preparation of novel aromatic compounds. 1993,65(1), 47-56. 91. Lai, Yee Hing; Chen, Pu; Peck, Thian Guan. Dihydropyrenes: further insight into effects of annulenoannelation, benzannelation, conjugation and isoannelation. 1993,65(1), 81-7. 92. Murata, Ichiro. Novel bonding structure of some nonalternant polycyclic systems. 1993,65(1),97-103. 93. Rabinovitz, Mordecai; Ayalon, h i . a-Conjugated polycyclic anions; interplay between topology, electronic structure and patterns of charge distribution. 1993,65(1), 111-18. 94. Girreser, Ulrich; Giuffrida, Daniele; Kohnke, Franz H.; Mathias, John P.; Philp, Douglas; Stoddart, J. Fraser. The structure-directed synthesis of cyclacene and polyacene derivatives. 1993,65(1), 119-25. 95. Vogel, Emanuel. The porphyrins from the ”annulene chemist’s” perspective. 1993,65(1), 143-52. 96. Vollhardt, K. Peter C. Thephenylenes. 1993,65(1), 153-56. 97. Yamamoto, Koji. Extended systems of closed helicene. Synthesis and characterization of [71and l7.71circulene. 1993,65(1),157-63. 98. Danil de Namor, Angela F. Thermodynamics of supramolecular systems: recent developments. 1993, 65(2), 193-202. 99. Van Dienst, Erik; Bakker, Wouter I. Iwema; Engbersen, Johan F. J.; Verboom, Willem; Reinhoudt, David N. Calixarenes, chemical chameleons. 1993,65(3), 387-92. 100. Sessler, Jonathan L.; Cyr, Michael; Furuta, Hiroyuki;Kral, Vladimir; Mody, Tarak; Morishima,Takashi; Shionoya, Mitsuhiko; Weghorn, Steven. Anion binding: anewdirectionin porphyrin-related research. 1993,65(3), 393-8. 101. Boehmer, Volker; Vogt, Walter. Calix[4larenes, bridged at the upper rim. 1993,65(3),403-8. 102. Danil de Namor, Angela F.; Blackett, Peter M.; Garrido Pardo, Maria T.; Pacheco Tanaka, David A,; Sueros Velarde, Felix J.; Cabaleiro, Mercedes C. From molecules to electrolytes. Electrochemical and thermodynamic aspects of the interaction of phenol- and resorcinol-based calixarenes with amines. 1993,65(3),415-22. 103. Holdt, H. J. Thiacrown compounds with 1,2dicyano-1,2-dithioetheneunits. 1993,65(3),477-82. 104. Jedlinski, Z. Alkali metal supramolecular complexes and their significance in organic chemistry. 1993, 65(3), 483-8. 105. Isnin, Rahimah; Kaifer, Angel E. A new approach to cyclodextrin-based rotaxanes. 1993,65(3), 495-8. 106. Krakowiak, Krzysztof E.; Bradshaw, Jerald S.; An, Haoyun; Izatt, Reed M. Simple methods for the preparation of cryptands. 1993,65(3), 511-14. 107. Luening, Ulrich; Baumstark, Roland; Wangnick, Carsten; Mueller, Michael; Schyja, Wolfgang; Gerst, Matthias; Gelbert, Markus. Concave reagents. 1993, 65(3), 527-32. 108. Cacciapaglia,Roberta; Mandolini, Luigi. Specific transition state stabilization by metal ions in reactions of functionalized crown ethers. 1993,65(3),533-8.
Recent Reviews 109. Choi, Heung Jin; Cram, Donald J.; Knobler, Carolyn B.; Maverick, Emily F. Characterization of cavities in carcerands. 1993,65(3),539-43. 110. Bachi, Mario D.; Balanov, Anna; Bar-Ner, Nira; Bosch, Eric; Denenmark, Daniella; Mizhiritskii, Michael. Synthesis of nonaromatic heterocyclic compoundsthrough free-radical reactions. 1993,65(4),595-601. 111. Barton, Derek H. R.; Parekh, Shyamal I. Ligand coupling based on heteroatom chemistry. 1993,65(4),60310. 112. Bestmann, H. J. Syntheses and reactionsof monoand polyelementorganic compounds. 1993,65(4), 61720. 113. Bickelhaupt, Friedrich. Carbenoid routes to substituted phosphaalkenes and phosphabenzenes. 1993, 65(4),621-4. 114. Garbesi, Anna; Gottarelli, Giovanni; Mariani, Paolo; Spada, Gian Piero. Oligodeoxyguanylates: a case of self-assembly leading to lyotropic liquid crystals. 1993, 65(4), 641-6. 115. Freeman, Richard; Haynes, Richard K.; Loughlin, Wendy A.; Mitchell, Craig; Stokes, John V. Synthetic utilization of highly stereoselective conjugate addition reactions of phosphorus and sulfur stabilized allylic carbanions. 1993,65(4), 647-54. 116. Imamoto, Tsuneo. Synthesis and reactions of new phosphine-boranes. 1993,65(4),655-60. 117. Kim, Yong Hae; Lim, Sang Chul; Kim, Kyung Su. Activation of superoxide: application of peroxysulfur intermediates to organic synthesis. 1993, 65(4), 661-6. 118. Marino, J. P. Asymmetric synthesis via optically active vinyl sulfoxides. 1993,65(4),667-74. 119. Nagase, Shigeru. Theoretical study of heteroatomcontaining compounds. From aromatic and polycyclic molecules to hollow cage clusters. 1993, 65(4), 675-82. 120. Schmidbaur, Hubert. Some new concepts in the chemistry of the p-block elements. 1993,65(4), 691-8. 121. Sonoda,Noboru. Selenium-assisted carbonylation with carbon monoxide. 1993,65(4),699-706. 122. Suska, Alina; Grajkowski,Andrzej; Wilk, Andrzej; Uznanski, Bogdan; Blaszczyk, Jerzy; Wieczorek, Michal; Stec, Wojciech J. Antisense oligonucleotides: stereocontrolled synthesis of phosphorothioate oligonucleotides. 1993,65(4),707-14. 123. Vasella, Andrea. A new approach to the synthesis of glycosides. 1993,65(4),731-52. 124. Ito, Yukishige; Gaudino, John J.; Paulson, James C. Synthesis of bioactive sialosides. 1993,65(4),753-62. 125. Kishi, Yoshito. Preferred solution conformation of marine natural product palytoxin and of C-glycosides and their parent glycosides. 1993,65(4),771-8. 126. Fraser-Reid, Bert; Merritt, J. Robert; Handlon, Anthony L.; Andrews, C. Webster. The chemistry of N-pentenyl glycosides: synthetic, theoretical, and mechanistic ramifications. 1993,65(4), 779-86. 127. Conrad, H. E. Dissection of heparin-past and future. 1993,65(4), 787-91. 128. Goto, Fumitaka; Ogawa, Tomoya. Recent aspects of glycoconjugate synthesis: a synthetic approach to the linkage region of proteoglycans. 1993,65(4), 793-801. 129. Saenger, W.;Niemann, C.; Herbst, R.; Hinrichs, W.; Steiner, T. Crystal structures of linear and cyclic oligosaccharides: an overview. 1993,65(4), 809-17. 130. Biemann, Klaus. Analytical techniques for trace organic compounds-IV. Tandem mass spectrometry for organic trace analysis. 1993,65(5), 1021-7.
J. Org. Chem., Vol. 58,No.20, 1993 5565 Recueil des Travaux Chimiques des Pays-Bas 131. Li, Haifang; Le Noble, William J. Competing concepts in electronic control of face selection. 1992, 111(5), 199-210. 132. Ott, Martin A.; Noordik, Jan H. Computer tools for reaction retrieval and synthesis planning in organic chemistry. A brief review of their history, methods, and programs. 1992,111(6), 239-46. 133. Dengler, A& Fontain, Eric; Knauer, Michael; Stein, Natalie; Ugi, Ivar. Competing concepts in CAOS. 1992, 111(6), 262-9. 134. Gasteiger, J.; Ihlenfeldt, W. D.; Rose, P. A collection of computer methods for synthesis design and reaction prediction. 1992,111(6), 270-90. 135. Dogane, I.; Takabatake, T.; Bersohn, M. Computer-executed synthesis planning, a progress report. 1992, 111(6), 291-6. 136. Hendrickson, James B. Descriptions of reactions: their logic and applications. 1992,111(6),324-35. 137. Koomen, G. J. Synthesisand biological properties of selected nucleoside analogs. 1993,112(2),51-65. 138. Verweij, Jan; de, Vroom Erik. Industrial transformations of penicillins and cephalosporins. 1993,112(2), 66-81. Russian Chemical Reviews 139. Akulov, P. Kinetic isotope effects in the enzymic reactions of tritium- and deuterium-containingsubstrata. 1992,61(10),999. 140. Chvertkina, L. V.; Khoklov, P. S.;Mironov, V. F. Phosphorus derivatives of salicylicacid. 1992,61(lo),1009. 141. Turuta, A. M.; Voishvillo, N. E.; Kamernetskii, A. V. Microbiological hydroxylation of 5a-H-steroids. 1992, 61(lo),1033. 142. Gatilov, Yu. V.; Barkhash, V. A. Investigation of molecular carbonium ion rearrangements by the molecular mechanics methods. 1992,61(11),1077. 143. Stadnichuk, M. D.;Voropaeva, T. I. Siliconcontaining 1,3-alkenynes and more unsaturated compounds. 1992,61(11),1091. 144. Krylov, 0.V. The partial catalytic oxidation of methane to give oxygen-containing compounds. 1992, 61(11),1118. 145. Kharitonov, A. S.; Sobolev, V. I.; Panov, G. I. Hydroxylatyion of aromatic compoundswith nitrous oxide. New possibilities of oxidative catalysts on zeolites. 1992, 61(11),1130. 146. Sadova, N. I.; Khaikin, L. S.; Vilkov, L. V. Some problems in the stereochemistry of nitrogen compounds in the gas phase. 1992,61(12), 1169. 147. Baranov, G. M.; Perekalin, V. V. Aliphatic organophosphorus nitro-compounds. 1992,61(12),1220. Science (Washington, D.C. 1883-) 148. Noyori, Ryoji; Suzuki, Masaaki. Organic synthesis of prostaglandins: advancing biology. 1993,259(5091),
44-5. 149. Nugent, William A,; RajanBabu, T. V.;Burk, Mark J. Beyond nature’s chiral pool: enantioselective catalysis in industry. 1993,259(5094),479-83. 150. Casey, Charles P. Organorhenium chemistry. 1993,259(5101),1552-8. 151. Marshall, W. S.;Caruthers, M. H. Phosphorodithioate DNA as a potential therapeutic drug. 1993, 259(5101), 1564-70.
5666 J. Org. Chem., Vol. 58, No. 20, 1993
Recent Reviews
Sulfur Reports 152. Trofimov, B. A.; Sokolyanskaya, L. V.; Senning, A. Divinyl disulfides: synthesis and properties. 1992, 12(1), 1-50. 153. Pyne, Stephen G. Diastereoselective reactions of sulfoximines. 1992, 12(1), 57-89. 154. Usov, V. A.; Timokhina, L. V.; Voronkov, M. G.
Thioformyl compounds. Synthesis, structure and properties. 1992, 12(2), 95-158. 155. Jaeger, L.; Koehler, H. Pseudochalcogens. 1992, 12(2), 159-212. 156. Drabowicz, Jozef; Kielbasinski,Piotr; Lyzwa,Piotr.
Stereoselective reactions at the a-carbon atom in organosulfur compounds. 1992,12(2), 213-96. 157. Brillon, Denis. Recent developments in the area of thionation methods and related synthetic applications. 1992, 12(2), 297-338. 158. Ghosh, Tirthankar. Reaction of carbenes with divalent sulfur compounds. 1992,12(2), 339-57. 159. Rao, V. Pushkara. The photoreactivity of thiocarbonyl compounds. 1992,12(2), 359-403. 160. Le Guillanton, Georges. Electrochemical activa-
tion of sulfur in organic solvents-new syntheses of thioorganic compounds with a sacrificial carbon-sulfur electrode. 1992, 12(2), 405-35.
Synlett 161. Uno, Hidemitsu; Suzukib, Hitomi. Nucleophilic perfluoroalkylation using perfluoroalkyllithiums. 1993, (2), 91-6. 162. Brook, Michael A.; Henry, Courtney; Jueschkke,
Ralf; Modi, Pankaj. Balancing leaving group ability and the @-effect:exploring the synthetic utility of chlorosilyl groups. 1993, (2), 97-104. 163. Bennetau, Bernard; Dunogues, Jacques. Unusual electrophilic substitution in the aromatic series via organosilicon intermediates. 1993, (31, 171-6. 164. Lautens, Mark. Ring opening reactions of oxabicyclic compounds as a route to cyclic and acyclic compounds with multiple stereocenters. 1993, (31, 177-85. 166. Golebiowski, Adam; Jurczak, Janusz. a-Amino@-hydroxyacids in the total synthesis of amino sugars. 1993, (4), 241-5. 166. Black, David St. C. New dimensions in indole chemistry: from ligand design to natural products. 1993, (4), 246-52.
Synthesis 167. Zimmer, Reinhold. Alkoxydlenes-building blocks in organic synthesis. 1993, (21, 165-78. 168. Campbell, M. M.; Sainsbury, M.; Searle,P. A. The
biosynthesis and synthesis of shikimic acid, chorismicacid, and related compounds. 1993, (21, 179-93.
169. Albini, Angelo. Synthetic utility of amine N-oxides. 1993, (3), 263-77. 170. Luh, Tien-Yau; Wong, Ken-Tsung. Silyl-substituted conjugated dienes: versatile building blocks of organic synthesis. 1993, (41, 349-70.
Tetrahedron 171. Beaucage, Serge L.; Iyer, Radhakrishnan P. The functionalization of oligonucleotidesvia phosphoramidite derivatives. Tetrahedron. 1993,49(10), 1925-63. 172. Gorbatenko, Victor I. Chemistry of chlorocarbonyl isocyanate. 1993,49(16), 3227-57. 173. Salomon, Claudio,; Mata, Ernesto G.. Recent developments in chemical deprotection of ester functional groups. 1993,49(18), 3691-3748. Topics in Current Chemistry 174. Zamaraev, K. I.; Khairutdiiov, R. F. Photoinduced electron tunneling reactions in chemistry and biology. 1992, 163 (Photoinduced Electron Transfer IV) 1-94. 175. Suppan, Paul. The Marcus inverted region. 1992, 163 (Photoinduced Electron Transfer IV), 95-130 176. Roth, Heinz D. Structure and reactivity of organic radical cations. 1992,163 (PhotoinducedElectron Transfer IV), 131-245. 177. Kohnke, Franz H.; Mathias, John P.; Stoddart, J. Fraser. Substrate-directed synthesis: the rapid assembly of novel macropolycyclic structures via stereoregularDielsAlder oligomerization. 1993,165 (Supramolecular Chemistry I-Directed Synthesis and Molecular Recognition), 1-69. 178. Zimmerman, Steven C. Rigid molecular tweezers as hosts for the complexation of neutral guests. 1993,165
(Supramolecular Chemistry I-Directed Synthesis and Molecular Recognition), 71-102. 179. Collet, AndrB; Dutasta, Jean-Pierre; Lozach, BBnBdicte; Canceill, Josette. Cyclotriveratrylenes and cryptophanes: their synthesis and applications to hostguest chemistry and to the design of new materials. 1993, 165 (SupramolecularChemistry I-Directed Synthesis and Molecular Recognition), 103-129. 180. Chambron, Jean-Claude; Dietrich-Buchecker, Christiane; Sauvage, Jean-Pierre. From clasical chirality to topologically chiral catenands and knots. 1993, 165 (Supramolecular Chemistry I-Directed Synthesis and Molecular Recognition), 131-162. 181. Misumi, Soichi. Recognitory coloration of cations with chromocarcerands. 1993,165 (Supramolecular Chemistry I-Directed Synthesis and Molecular Recognition), 163-192. 182. Tomalia, Donald A.; Durst, H. Dupont. Genea-
logically directed synthesis: starburst/cascade dendrimers and hyperbranched structures. 1993,165 (Supramolecular Chemistry I-Directed Synthesis and Molecular Recognition), 193-313.
Contributed Volumes Advances in the Use of Synthons in Organic Chemistry. Volume 1. Alessandro Dondoni, Ed., Jai Press: Grennwich, CT, 1993. 183. Dondoni, Alessandro; Colombo, Lino. New formyl anion and cation equivalents. 184. Shioiri, Takayuki; Aoyama, Toyohiko. Trimeth-
ylsilyldiazomethane. A versatile synthon for organic chemistry. 185. Saalfrank, Rolf W.; Burak, Roman. Form pushpull-substituted allenes to tetra-nuclear chelate complexes via spontaneous self-assembly. 186. Danieli, Bruno; Lesma, Giordano; Passarella, Daniele; Riva, Sergio. Chiral synthons via enzymemediated asymmetrization of meso-compounds.
J. Org. Chem., Vol. 58,No. 20, 1993 5567
Recent Reviews
Monographs 187. Aitken, R. A.; Kilhyi, S. N., Eds. Asymmetric Synthesis. Blackie Academic & Professional/Chapman and Hall: London, 1992. 188. Ando, Wataru, Ed. Organic Peroxides. Wiley: Chichester, U.K., 1992. 189. Anon. The Brandon Amino Acid and Peptide Guide. Brandon Associates, Merrimack, NH, 1992. 190. BeMiller, James N.; Whistler, Roy L.; Shaw, Derik H, Eds. Lipopolysaccharides, Separation and Analysis, Glycosylated Polymers (Methods in Carbohydrate Chemistry, Vol. 9). Wiley: New York, 1993. 191. Billups, W. Edward; Ciufolini, Marco A., Eds. Buckminsterfullerenenes. VCH New York, 1993. 192. Bradshaw, Jerald S.; Krakowiak, Krzysztof E.; Izatt, Reed M. Aza-crown Macrocycles. (Chemistry of Heterocyclic Compounds, Vol. 51). Wiley: New York, 1993. 193. Cintas, P. Activated Metals in Organic Synthesis. CRC Press: Boca Raton, FL, 1993. 194. Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd ed. VCH: New York, 1993. 195. Furin, G. G. Synthetic Aspects of the Fluorination of Organic Compounds. Harwood Academic Publ.: Reading, Berkshire, U.K., 1991. 196. Goldberg, Yuri. Phase Transfer Catalysis. Selected Problems and Applications. Gordon and Breach: Philadelphia, PA, 1992. 197. Kagan, Jacques. Organic Photochemistry. Principles and Applications. Academic: London, 1993. 198. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules. VCH: New York, 1993. 199. Mark, Herman. From Small Molecules to Large: A Century of Progress. (Profiles, Pathways and Dreams: Autobiographies of Eminent Chemists, Jeffrey I. Seeman, Ed.) American Chemical Society: Washington, DC, 1993.
200. Oki, Michinori. Chemistry of Rotational Isomers. (Reactivity and Structure, Vol. 31). Springer-Verlag: Berlin, Germany, 1993. 201. Page, Michael I.,Ed. The Chemistry of P-Lactams. Blackie Academic & Professional/Chapman and Hall: London, 1992. 202. Patai, Saul, Ed. Supplement B: The Chemistry of Acid Derivatives, Vol. 2, Part 2 (The Chemistry of Functional Groups). Wiley: Chichester, U.K., 1992. 203. Peters, K. E.; Moldowan, J. M. The Biomarker Guide: Interpreting Molecular Fossils in Petroleum and Ancient Sediments. Prentice Hall: Englewood Cliff, NJ, 1993. 204. Rahman, Atta-Ur; Basha, Fatima A., Eds. Studies in Natural Products Chemistry, Vol. 13: Bioactive Natural Products, Part A. Elsevier: Amsterdam, The Netherlands, 1993. 205. Rahman, Atta-Ur, Ed. Studies in Natural Products Chemistry, Vol. 11: Stereoselective Synthesis, Part G. Elsevier: Amsterdam, The Netherlands, 1992. 206. Rahman, Atta-Ur; Shah, Zahir. Stereoselective Synthesis in Organic Chemistry. Springer-Verlag: Berlin, 1993. 207. Sandler, Stanley R.; Karo, Wolf. Sourcebook of Advanced Organic Laboratory Preparations. Academic: San Diego, CA, 1992. 208. Smith, K., Ed. Solid Supports and Catalysts in Organic Synthesis. Ellis Horwood: Chichester, U.K., 1992. 209. Strukul, Georgio, Ed. Catalytic Oxidations with Hydrogen Peroxide as Oxidant. Kluwer Academic Publ.: Dordrecht, The Netherlands, 1992. 210. Weissermel, Klaus; Arpe, Hans-Jiirgen. Industrial Organic Chemistry, 2nd ed.; VCH: New York, 1993.
Index Acid derivatives, book, 202 Acridone alkaloids, 73 N-Acyliiidazoles, hydrolysis, 13 Alcohols, optically active, 87 Alkali metal supramolecular complexes, 104 Alkaloids, 65, 70, 71, 73, 76, 85 synthesis, 65 1,3-Alkenynes,silicon-containing, 143 Alkoxyallenes, 167 Allenes, push-pull-substituted, 185 Allylic carbanions, stabilized, 115 Allylic substitution, enantioselective, 35 Amide hydrolysis, 13 Amination, of heterocycles, 22 Amino acids, book, 189 a-Amino-&hydroxy acids, 165 Amine N-oxides, in synthesis, 169 Amino sugara, synthesis, 165 Analysis, trace organic compounds, 130 Anion binding, 100 Anions, weakly coordinating, 41 Annelation, 91 to 1,2-diazines, 55 Annulene chemistry and porphyrins, 95
Antisense oligonucleotides, 122 Aromatic compounds, hydroxylation, 145 novel, 90 substitution, 163 theory, 119 Asymmetric catalysis, 14 Asymmetric synthesis, absolute, 36 book, 187 carbonic anhydrase inhibitor, 64 catalytic, 87 via sulfoxides, 118 Asymmetrization, of meso compounds,186 Aza sugars, synthesis, 4 Azaaromatic compounds, nitro, 22 Azadiindoles, 57 Azadirachtin, 74 Azides, heterocyclic, 26 Benzannelation, 91 1,5-Benzodiazepines, annulated, 59, 60 Benzofuroxans, rearrangements, 54 Benzothiazepines, 68 Binding, of anions, 100 Biomarkers, 203 Biopolymers,physiologically important, 34 d- and f-Block elements, 44
C-N Bond breaking, 13 Bond energies, in solution, 10 Bond-stretch isomerism, reevaluation, 39 Boron compounds, 24 Buckminsterfullerenes, book, 191 Cage clusters, hollow, 119 Cage effects, gas-phaee analogs, 11 Calixarenes, 99 bridged, 101 electrochemistry, 102 interaction with amines, 102 CAOS, 133 Cappedophanes, 89 Carbenes, in matrixes, 51 reactions,withsulfurcompounds,158
Carbenoids, in phosphorus compound synthesis, 113 Carbohydrates, as chiral auxiliaries, 32 Carbonmonoxide, carbonylationwith, 121 Carbonicanhydrase inhibitor, asymmetric synthesis, 64 Carbonium ion rearrangements, 142 Carbonylation, with CO, 121 Carborane metal complexes, 44 Carcerands, cavities of, 109
