An example of substitution proceeding with retention in the S RN1 reaction. Trapping of a pyramidal benzylic radical by benzenethiolate ion

Abstract
The SRN1 reaction of c-4-t-butyl-c-2-methyl-r-1-nitro-1-p-nitrophenylcyclohexane with sodium benzenethiolate in hexamethylphosphoramide, which proceeds with retention of configuration at C-1 at relatively high thiolate concentrations, and with competing inversion and retention at lower thiolate concentrations, implicates the formation and trapping of a pyramidal benzylic radical.

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