The products of an imino Diels-Alder reaction with 2- trimethylsilyloxycyclohexadiene: Synthesis, X-ray crystal structures, and mechanistic implications

Timothy N. Birkinshaw; Alethea B. Tabor; Andrew B. Holmes; Perry Kaye; Peter M. Mayne; Paul R. Raithby

doi:10.1039/C39880001599

The products of an imino Diels-Alder reaction with 2- trimethylsilyloxycyclohexadiene: Synthesis, X-ray crystal structures, and mechanistic implications

Timothy N. Birkinshaw, Alethea B. Tabor, Andrew B. Holmes, Perry Kaye, Peter M. Mayne, Paul R. Raithby

University of Cambridge

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

Abstract

The reaction of the N-tosyl imino-ester (1) with 2- trimethylsilyloxycyclohexadiene (2) followed by acidic work-up shows a divergence in pathways: at low temperature in polar solvents the cyclohexenones (5) and (6) (X-ray) are favoured, whereas at higher temperatures the bicyclic ketones (3) and (4) (X-ray) are the predominant products.

Original language	English
Pages (from-to)	1599-1601
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	24
DOIs	https://doi.org/10.1039/C39880001599
Publication status	Published - 1988

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Molecular Medicine

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The products of an imino Diels-Alder reaction with 2- trimethylsilyloxycyclohexadiene: Synthesis, X-ray crystal structures, and mechanistic implications. / Birkinshaw, Timothy N.; Tabor, Alethea B.; Holmes, Andrew B. et al.
In: Journal of the Chemical Society, Chemical Communications, No. 24, 1988, p. 1599-1601.

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

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abstract = "The reaction of the N-tosyl imino-ester (1) with 2- trimethylsilyloxycyclohexadiene (2) followed by acidic work-up shows a divergence in pathways: at low temperature in polar solvents the cyclohexenones (5) and (6) (X-ray) are favoured, whereas at higher temperatures the bicyclic ketones (3) and (4) (X-ray) are the predominant products.",

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The products of an imino Diels-Alder reaction with 2- trimethylsilyloxycyclohexadiene: Synthesis, X-ray crystal structures, and mechanistic implications

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