Y. Taskesenligil et M. Balci, AN UNUSUAL ZINC-PROMOTED REDUCTIVE RETRO-WAGNER-MEERWEIN REARRANGEMENT, Turkish journal of chemistry, 20(4), 1996, pp. 335-340
Bromination and dehydrobromination of exocyclic olefin 8 resulted in t
he formation of bromomethylene compound 9 and Wagner-Meerwein rearrang
ement product 10. The dehydrobromination of 10 with potassium tert-but
oxide provided the corresponding bromomethyl compound 11 in high yield
. Reaction of 11 with Zn-Cu couple in methanol afforded the methyl der
ivative 12 and the parent olefin 8. The unusual formation mechanism of
8 has been discussed in term of a reductive retro-Wagner-Meerwein rea
rrangement.