The Cope rearrangement of gem-dimethyl substituted divinylcyclopropanes

Jonathan D Osler; William P Unsworth; Richard J K Taylor

doi:10.1039/c3ob41617h

The Cope rearrangement of gem-dimethyl substituted divinylcyclopropanes

Jonathan D Osler, William P Unsworth, Richard J K Taylor

Chemistry

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

Abstract

The reactivity of a range of substituted divinylcyclopropanes towards the thermal Cope rearrangement has been examined. The effects of gem-dimethyl substitution on the cyclopropane, the alkene geometry, the relative stereochemistry of the cyclopropane and the steric and electronic effects of a range of functional groups were all examined, and the methods developed were used to synthesise a range of functionalised 1,4-cycloheptadienes in high yields.

Original language	English
Pages (from-to)	7587-7594
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	43
DOIs	https://doi.org/10.1039/c3ob41617h
Publication status	Published - 7 Oct 2013

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10.1039/c3ob41617h

http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob41617h#!divAbstract

Cite this

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title = "The Cope rearrangement of gem-dimethyl substituted divinylcyclopropanes",

abstract = "The reactivity of a range of substituted divinylcyclopropanes towards the thermal Cope rearrangement has been examined. The effects of gem-dimethyl substitution on the cyclopropane, the alkene geometry, the relative stereochemistry of the cyclopropane and the steric and electronic effects of a range of functional groups were all examined, and the methods developed were used to synthesise a range of functionalised 1,4-cycloheptadienes in high yields.",

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AB - The reactivity of a range of substituted divinylcyclopropanes towards the thermal Cope rearrangement has been examined. The effects of gem-dimethyl substitution on the cyclopropane, the alkene geometry, the relative stereochemistry of the cyclopropane and the steric and electronic effects of a range of functional groups were all examined, and the methods developed were used to synthesise a range of functionalised 1,4-cycloheptadienes in high yields.

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DO - 10.1039/c3ob41617h

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