New PDF release: Alicyclic chemistry. Vol. 6 : a review of the literature

By M A McKervey, Chemical Society

ISBN-10: 0851866328

ISBN-13: 9780851866321

ISBN-10: 1847555497

ISBN-13: 9781847555496

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Krief, Tetrahedron Letters, 1976, 3911. Alicyclic Chemistry 38 acetals may be employed whereupon the stereospecific formation of cyclopropyl esters (149) occurs, but in even higher yield ( 8 0 4 5 % ) . -The electrochemical reduction of 1,3-diketones, PhCOCR',COR2 (R1 = H or alkyl, R2 = alkyl or aryl), leads to cyclopropane1,2-diols by a bielectronic process. 162However, in polar media ( M e 0 the adduct produced is the sterically least favoured form (150; endo-CO,Me) and its structure has been confirmed by X-ray methods.

Yamaguchi, K. Kawada, T. Okamoto, E. Egert, H. J. Linder, M. Braun, R. Dammann, M. Liesner, H. Neumann, and D. , p. 1589; R. W. Gray, C. B. Chapleo, T. Vergnani, and A. S. Dreiding, Helo. Chim. Act% 1976, 59, 1547; (c) H. Yamaguchi and T. Okamoto, Chem. and Pharm. Bull. (Japan), 1975, 23, 2907 (Chem. , 1976,84, 44 429). g. g. (198), with inversion of configuration, and under mild conditions, as illustrated for compound (199) in Scheme 24. 213The reaction between 1,1-dicyano-2,2-dimethylcyclopropaneand the enamine derived from pyrrolidine and cyclopentanone proceeds by a nucleophilic pathway with attack at C-3 of the cyclopropane ring; C-1-C-2 bond cleavage of the cyclopropane to give a 1,3-dipole is not Whereas the dibenzoylcyclopropane (200: R = H) Ph Ph Ph NH,NH, I 41)- Ph R=H Ph Ph or P:qL>- Ph 0 0 Ph, CH Ph Ph N-N ''' '13 Ph O P N-N h E.

Surpateanu, Tetrahedron Letters, 1976, 3081. R. J. Norstrom, H . E. Gunning, and 0. P. Strausz, J . Amer. Chem. , 1976,98, 1454. Alicyclic Chemistry 24 exclusive cleavage of the bond between the methylene- and difluoro-substituted carbon atoms. However, with added tetramethylethylene, the difluoromethylenetetramethylcyclopropane (77) produced is stable. '15 The process is believed to involve a biradical or zwitterionic intermediate and, in all cases examined, the product is the bicyclic system (80), although at Ph '=N Me R2 R' H (78) hv I R' [,or R2 I I H HvR3 c - hv Me Me' R2 R3 (81) Scbeme 7 A.

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Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976 by M A McKervey, Chemical Society

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