An example of substitution proceeding with retention in the SRN1 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.