The Journal of Organic Chemistry

The Preparation of 4-Pentenenitriles and 3, 4-Pentadienenitriles from N-(2-Alkenyl)-and N-(2-Alkynyl) amides

KC Brannock, RD Burpitt

Index: Brannock,K.C.; Burpitt,R.D. Journal of Organic Chemistry, 1965 , vol. 30, p. 2564 - 2565

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Citation Number: 21

Abstract

N-(2-Alkeny1) amides are converted to imino chlorides or imino chloride hydrochlorides with phosphorus (V) chloride or phosgene, respectively. These products, on treatment with a tertiary amine, give 4-pentenenitriles via a Claisen-type rearrangement. Since intermediates have not been isolated, it is not known whether the reaction proceeds through the formation of a discrete ketenimine or whether the process is a concerted one. The reaction appears ...