Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols

Stefano Menichetti; Charles J. M. Stirling

doi:10.1039/B109805E

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Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols†

Stefano Menichetti*^a and Charles J. M. Stirling^b

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* Corresponding authors

^a Dipartimento di Chimica Organica e Biologica, Università di Messina, Salita Sperone 31, Messina, I-98166, Italy
E-mail: menichet@isengard.unime.it

^b Department of Chemistry, University of Sheffield, Sheffield, UK

Abstract

A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3.

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DOI: https://doi.org/10.1039/B109805E
Article type: Paper
Submitted: 26 Oct 2001
Accepted: 12 Nov 2001
First published: 04 Dec 2001

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J. Chem. Soc., Perkin Trans. 1, 2002, 28-30

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Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols

S. Menichetti and C. J. M. Stirling, J. Chem. Soc., Perkin Trans. 1, 2002, 28 DOI: 10.1039/B109805E

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Journal of the Chemical Society, Perkin Transactions 1

Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols†

Abstract

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Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols

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