Issue 3, 1981

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1981, 79-80

An example of substitution proceeding with retention in the SRN1 reaction. Trapping of a pyramidal benzylic radical by benzenethiolate ion

R. K. Norris and R. J. Smyth-King, J. Chem. Soc., Chem. Commun., 1981, 79 DOI: 10.1039/C39810000079

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