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By K H Overton

ISBN-10: 0851862667

ISBN-13: 9780851862668

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C. h I 10 : 3 1 \ : 62 : 24 Reagents: i, Zn-HOAc; ii, base; iii, LiAlH,. Scheme 12 leads only to exo-amines, while reduction with sodium in alcohol gives endoamines. '82 In' "' ''I A. Coulombeau and A . Rassat, Bull. chint. France, 1971, 505. A. Daniel and A . A . Pavia, B i d . Soc. chim. Frunce, 1971, 1060. N . B. Kupletskaya, G. V. Panova, Le Quang Lien, a n d A . P. fiz. , 197 1. 45, 707. A . P. Terent'ev, G. V . Panova, and 0. V . , 1971, 41, 476. ’ 83 (252) (253) Chromatography (especially on silica gel) of the aryl alcohols derived from Grignard reactions on camphor and other bicyclic ketones can give products formed by bond migration (254) or by dehydration (255), and since the reactions are stereoscopic and selective, Ramage et al.

Resonance, 1969, 1, 51. C. W. Jefford and U. ),1970, 24, 385. Y. Bessiere-Chretien and B. Meklati, Bull. chim. France, 1971, 2591. C. W. Jefford, personal communication. l,l]octane ring system has also been synthesized by Joulain and Rouessac, following a similar path to that used by Hatem and Waegell; their note described a number of other unsuccessful routes. O 0 Acetylation of pinane (77) (90 '/" cis) with acetyl chloride and aluminium chloride under Friedel-Crafts conditions leads to the same mixture of l-chloro2-acetylmenthanes (27 1) as is obtained in a similar reaction using menth-1-ene (103), through which the reaction is assumed to pass.

154 A synthesis of chiral ( -)-(7R)-8-deuteriobornadiene (204) follows the route shown in Scheme 7. The overall yield of (+)-9-deuteriobornylene (205) from (+)-camphor via the known (+)-9-bromocamphor (206) was 35%, and the 147 148 149 1so 151 152 153 1s4 V. Hach, R. W. Lockhart, E. C. McDonald, and D. M. Cartlidge, Canad. J. , 1971, 49, 1762. R. S. Cooke and G. D. Lyon, J. Amer. Chem. , 1971, 93, 3840. F. H . Allen and D. Rogers, J. Chem. Sac. ( B ) , 1971, 632. L. Bartlett, D. N . Kirk, W. Klyne, S.

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A Review of the literature published between September 1970 and August 1971 by K H Overton

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