The Journal of Organic Chemistry

Arylation of several carbanions by the SRN1 mechanism

RA Rossi, JF Bunnett

Index: Rossi,R.A.; Bunnett,J.F. Journal of Organic Chemistry, 1973 , vol. 38, p. 3020 - 3025

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Citation Number: 56

Abstract

The carbanions derived from 1, 3-pentadiene, l-(p-anisyl) propene, indene, fluorene, 2- butanone, and 3-methyl-2-butanone are phenylated by treating them with bromobenzene and sodium or potassium metal in liquid ammonia. The enolate ions of the two ketones are also phenylated by photostimulated reaction with bromo-or iodobenxene. By either method, 2-butanone is phenylated principally at the 3 position and 3-methyl-2-butanone mainly at ...