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

César Alejandro Urbina Blanco; Maciej Skibinski; David O'Hagan; Steven Patrick Nolan

doi:10.1039/c3cc44312d

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

César Alejandro Urbina Blanco, Maciej Skibinski, David O'Hagan, Steven Patrick Nolan

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	7201-7203
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	65
Early online date	4 Jul 2013
DOIs	https://doi.org/10.1039/c3cc44312d
Publication status	Published - 21 Aug 2013

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10.1039/c3cc44312d

Cite this

@article{b5e37ab5bc704f56b08d8fd1a5df2187,

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

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.",

author = "\{Urbina Blanco\}, \{C{\'e}sar Alejandro\} and Maciej Skibinski and David O'Hagan and Nolan, \{Steven Patrick\}",

note = "SPN thanks the European Community Seventh Framework Programme (FP7/2007–2013) under grant agreement no. CP-FP 211468-2 EUMET and the ERC (Advanced Investigator Grant-FUNCAT) for support of this work. SPN is a Royal Society Wolfson Research Merit Award holder. DOH thanks the ERC for an Advanced Investigator Grant and is a Royal Society Wolfson Research Merit Award holder.",

year = "2013",

month = aug,

day = "21",

doi = "10.1039/c3cc44312d",

language = "English",

volume = "49",

pages = "7201--7203",

journal = "Chemical Communications",

issn = "1359-7345",