An example of substitution proceeding with retention in the S RN1 reaction. Trapping of a pyramidal benzylic radical by benzenethiolate ion
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 3,p. 79-80
- https://doi.org/10.1039/c39810000079
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.Keywords
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