REGIOCHEMICAL CONTROL IN THE 1,2-CARBONYL TRANSPOSITION OF α,α'-DIMETHYLENE SYSTEMS THROUGH REGIOSELECTIVE SULFENYLATION OF TOSYLHYDRAZONE DIANIONS

Article abstract of DOI:10.1246/cl.1980.931

The regiochemical outcomes are described in the 1,2-carbonyl shift of α,α'-dimethylene systems which relies upon the regioselective sulfenylation of tosylhydrazone dianions leading to the enol thioethers of transposed ketones.Notably, a high regiospecificity was obtained with β-methyl- and β,β-dimethylcyclohexanone without any attempts to separate the stereoisomers of the hydrazones.