Issue 24, 1988

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

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1988, 1599-1601

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

T. N. Birkinshaw, A. B. Tabor, A. B. Holmes, P. Kaye, P. M. Mayne and P. R. Raithby, J. Chem. Soc., Chem. Commun., 1988, 1599 DOI: 10.1039/C39880001599

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