Solvolysis of optically active 4-methylcyclohexylidenemethyl triflate: Evidence against a primary vinyl cation as an intermediate

Citation
M. Fujita et al., Solvolysis of optically active 4-methylcyclohexylidenemethyl triflate: Evidence against a primary vinyl cation as an intermediate, CHEM LETT, (8), 2001, pp. 806-807
Citations number
25
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
0366-7022 → ACNP
Issue
8
Year of publication
2001
Pages
806 - 807
Database
ISI
SICI code
0366-7022(20010805):8<806:SOOA4T>2.0.ZU;2-P
Abstract
Solvolysis of (R)-4-methylcyclohexylidenemethyl triflate in aqueous methano l at 140 degreesC gave stereospecifically (R)-4-methyl-cycloheptanone to de finitively rule out intermediate formation of the achiral primary vinyl cat ion. The rearrangement must occur via concerted a-bond participation.