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

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Abstract
The reactions of a series of α-substituted p-nitrobenzyl chlorides, p- NO2C6H4CH(Cl)R (R = Me, Et, Prt, But), with the lithium salt of 2- nitropropane in dimethyl sulphoxide and dimethylformamide have been studied. When R = Me or Et, competing SRN1 and SN2 processes take place, giving C- and O-alkylated products respectively. In the more sterically hindered cases where R = Pri or But, the only reaction taking place has been shown to be an SRN1 reaction with exclusive O-alkylation. These observations indicate that the SRN1 reaction is prone to steric hindrance, and that radical alkylation of the ambident nitronate ion occurs on the more accessible oxygen atom in sterically hindered situations.

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