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.

DOI

First Page

335

Last Page

340

Recommended Citation

TAŞKESENLİGİL, Y, & BALCI, M (1996). An Unusual Zinc-Promoted Reductive Retro-Wagner-Meerwein Rearrangement. Turkish Journal of Chemistry 20 (4): 335-340. https://doi.org/-

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