AN UNUSUAL ZINC-PROMOTED REDUCTIVE RETRO-WAGNER-MEERWEIN REARRANGEMENT

Authors
TASKESENLIGIL Y BALCI M
Citation
Y. Taskesenligil et M. Balci, AN UNUSUAL ZINC-PROMOTED REDUCTIVE RETRO-WAGNER-MEERWEIN REARRANGEMENT, Turkish journal of chemistry, 20(4), 1996, pp. 335-340
Citations number
17
Categorie Soggetti
Chemistry,"Engineering, Chemical
Journal title
Turkish journal of chemistry → ACNP
ISSN journal
13000527
Volume
20
Issue
4
Year of publication
1996
Pages
335 - 340
Database
ISI
SICI code
1300-0527(1996)20:4<335:AUZRRR>2.0.ZU;2-1
Abstract
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.