Issue 65, 2013
From the journal:

Chemical Communications

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

César A. Urbina-Blanco,‡a   Maciej Skibiński,‡a   David O'Hagan*a  and  Steven P. Nolan*a  

* Corresponding authors

a EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, UK
E-mail: snolan@st-andrews.ac.uk, do1@st-andrews.ac.uk

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C3CC44312D
Article type
Communication
Submitted
07 Jun 2013
Accepted
04 Jul 2013
First published
04 Jul 2013

Chem. Commun., 2013,49, 7201-7203

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

C. A. Urbina-Blanco, M. Skibiński, D. O'Hagan and S. P. Nolan, Chem. Commun., 2013, 49, 7201 DOI: 10.1039/C3CC44312D

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