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
Recommended Citation
TAŞKESENLİGİL, Yavuz and BALCI, Metin (1996) "An Unusual Zinc-Promoted Reductive Retro-Wagner-Meerwein Rearrangement," Turkish Journal of Chemistry: Vol. 20: No. 4, Article 11. Available at: https://journals.tubitak.gov.tr/chem/vol20/iss4/11
