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UBC Theses and Dissertations

The synthesis of anti-8-tricyclo [3.2.1.0 2,4] octanol and solvolysis of its p-bromobenzenes-ulphonyl derivative Wells, June I.

Abstract

The synthesis of anti-8-tricyclo [3.2.1.0[superscript 2,4]] octanol has been carried out by the cuprous chloride catalysed reaction of diazomethane on anti-7-norbornenol. X-ray crystallographic analysis of the p-bromo-benzene sulphonyl (brosylate) derivative has unambiguously shown the cyclopropyl group to be exo. Methylene addition to norbornene and 7-norbornadienyl acetate was achieved by the above method; for the latter, the two isomers whose presence was detected by n.m.r. could not be separated. The slow rate of the acetolysis of the brosylate of anti-8-tricyclo [3.2.1.0[superscript 2,4]] octanol suggests that this derivative resembles 7-norbornyl brosylate in solvolysis reactions, rather than anti-7-norbornenyl brosylate. Enthalphy of activation calculated for the tricyclic brosylate solvolysis is of the same order as that for the 7-norbornyl case. Product studies on material isolated from samples solvolysed up to the half life of the brosylate suggest the first product probably is anti-8-tricyclo [3.2.1.0[superscript 2,4] octanyl acetate. Prolonged solvolysis conditions result in a variety of products in which the cyclopropyl group has rearranged. The structures of these products could not be determined.

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