Australian Journal of Chemistry

The effect of steric hindrance on the SRN1 reaction of some α-Alkyl-p-nitrobenzyl chlorides

RK Norris, D Randles

Index: Norris,R.K.; Randles,D. Australian Journal of Chemistry, 1976 , vol. 29, p. 2621 - 2629

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Citation Number: 11

Abstract

Abstract The reactions of a series of α-substituted p-nitrobenzyl chlorides, p-NO 2 C 6 H 4 CH (Cl) R (R= Me, Et, Pr t, Bu t), with the lithium salt of 2-nitropropane in dimethyl sulphoxide and dimethylformamide have been studied. When R= Me or Et, competing S RN 1 and SN 2 processes take place, giving C-and O-alkylated products respectively. In the more sterically hindered cases where R= Pr i or Bu t, the only reaction taking place has been shown to be ...