The first example of a transoid amide (imide) in an eight-membered lactam

P. Andrew Evans; Andrew B. Holmes; Ian Collins; Paul R. Raithby; Keith Russell

doi:10.1039/C39950002325

The first example of a transoid amide (imide) in an eight-membered lactam

P. Andrew Evans, Andrew B. Holmes, Ian Collins, Paul R. Raithby, Keith Russell

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

Abstract

The Claisen rearrangement of the ketene aminal derived by selenoxide elimination of the seleno-aminal 1 in refluxing toluene in the presence of dihydropyran yields the expected unsaturated eight-membered lactam derivative 3, as well as two unexpected products 7a and 7b; the major product 7a (resulting from a selenium re-addition reaction) was shown by X-ray crystallography to be a highly distorted transoid amide (imide) with the largest p-orbital distortion (τ=50.6°) recorded for a cyclic amide.

Original language	English
Pages (from-to)	2325-2326
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	22
DOIs	https://doi.org/10.1039/C39950002325
Publication status	Published - 1995

ASJC Scopus subject areas

Molecular Medicine

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abstract = "The Claisen rearrangement of the ketene aminal derived by selenoxide elimination of the seleno-aminal 1 in refluxing toluene in the presence of dihydropyran yields the expected unsaturated eight-membered lactam derivative 3, as well as two unexpected products 7a and 7b; the major product 7a (resulting from a selenium re-addition reaction) was shown by X-ray crystallography to be a highly distorted transoid amide (imide) with the largest p-orbital distortion (τ=50.6°) recorded for a cyclic amide.",

author = "Evans, {P. Andrew} and Holmes, {Andrew B.} and Ian Collins and Raithby, {Paul R.} and Keith Russell",

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AU - Evans, P. Andrew

AU - Holmes, Andrew B.

AU - Collins, Ian

AU - Raithby, Paul R.

AU - Russell, Keith

PY - 1995

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AB - The Claisen rearrangement of the ketene aminal derived by selenoxide elimination of the seleno-aminal 1 in refluxing toluene in the presence of dihydropyran yields the expected unsaturated eight-membered lactam derivative 3, as well as two unexpected products 7a and 7b; the major product 7a (resulting from a selenium re-addition reaction) was shown by X-ray crystallography to be a highly distorted transoid amide (imide) with the largest p-orbital distortion (τ=50.6°) recorded for a cyclic amide.

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JF - Journal of the Chemical Society, Chemical Communications

IS - 22

ER -

The first example of a transoid amide (imide) in an eight-membered lactam

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