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Turkish Journal of Chemistry

DOI

-

Abstract

Bromination and dehydrobromination of exocyclic olefin {\bf 8} resulted in the formation of bromomethylene compound {\bf 9} and Wagner-Meerwein rearrangement product {\bf 10}. The dehydrobromination of {\bf 10} with potassium {\it tert}-butoxide provided the corresponding bromomethyl compound {\bf 11} in high yield. Reaction of {\bf 11} with Zn-Cu couple in methanol afforded the methyl derivative {\bf 12} and the parent olefin {\bf 8}. The unusual formation mechanism of {\bf 8} has been discussed in term of a reductive retro-Wagner-Meerwein rearrangement.

First Page

335

Last Page

340

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