Accelerating influence of the gem-difluoromethylene group in a ring-closing olefin metathesis reaction. A Thorpe-Ingold effect?

Autor: Urbina-Blanco CA; EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK., Skibiński M, O'Hagan D, Nolan SP
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2013 Aug 21; Vol. 49 (65), pp. 7201-3. Date of Electronic Publication: 2013 Jul 11.
DOI: 10.1039/c3cc44312d
Abstrakt: The gem-difluoromethylene (CF2) group significantly accelerates ring-closing metathesis of 1,8-nonadienes relative to the methylene (CH2) group demonstrating similar rate accelerations to that observed for the classic Thorpe-Ingold substituents, diester malonates and ketals.
Databáze: MEDLINE