Nitrogen Analogs of Ketenes. III. Formation of Hydroperoxides and Vinylamines by Reaction with Lithium Aluminum Hydride and Organometallic Reagents1, 2

CL Stevens, RJ Gasser

Index: Stevens; Gasser Journal of the American Chemical Society, 1957 , vol. 79, p. 6057,6061

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Citation Number: 12

Abstract

Reduction of diphenylketene-p-tolylimine (I) with lithium aluminum hydride gave the amino alcohol I1 by reaction via a hydroperoxide. The ketenimine I reacted with phenylmagnesium bromide to give a stable hydroperoxide I11 which could be reduced catalytically to the ketone imine IV or with lithium aluminum hydride to the amino alcohol V. Mesitylmagnesium bromide also yielded a stable hydroperoxide VI when allowed to react with I. ...