The influence of the nitro-group upon side-chain reactivity. Part IV. The inhibition of α-proton extraction from 4-nitrobenzyl chloride by the steric effect of methyl groups …

DM Doleib, Y Iskander

Index: Doleib,D.M.; Iskander,Y. Journal of the Chemical Society [Section] B: Physical Organic, 1967 , p. 1154 - 1158

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Citation Number: 2

Abstract

The fast α-proton extraction from 4-nitrobenzyl chloride by alkali in dioxan, leading to the formation of 4, 4′-dinitrostilbene by the α-E1cB mechanism (the rate-determining step is formation of a carbene intermediate), is greatly retarded by one methyl group in the 3- position and completely inhibited by two methyl groups in the 3-and 5-positions; instead, alcohols and ethers are formed by the SN2 displacement of the halogen by the alkali and ...