Unsaturated carbenes from primary vinyl triflates. II. Spin multiplicity via the stereochemistry of addition to olefins

PJ Stang, MG Mangum

Index: Stang,P.J.; Mangum,M.G. Journal of the American Chemical Society, 1975 , vol. 97, p. 1459 - 1464

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Citation Number: 30

Abstract

Abstract: The stereochemistry of addition of isopropylidenecarbene, generated from primary vinyl triflates, to olefins was investigated. Addition was found to be more than 98% stereoselective to cis-and trans-2-methoxy-2-butene and stereospecific to cis-and trans-2- butene indicating that the nascent carbene is a singlet. Dilution experiments with trans-2- butene and perfluorocyciobutane as the inert diluent strongly suggest that the singlet is ...

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