REACTIVITY OF CYCLOOCTENE DERIVED EPISULFONIUM IONS TOWARD NUCLEOPHILES AND THE COURSE OF SULFENYL HALIDE ADDITION TO CYCLOOCTENE

Article abstract of DOI:10.1016/0040-4020(80)85049-6

The reactions of the stable S-methylepisulfonium ions derived from cis-cyclooctene with various nucleophiles were found to proceed mainly as the attack at C atom of episulfonium ring in contrast to the previous data of Helmkamp et al.The course of the RSCl Ad_E-reaction with cyclooctene under the conditions of increased polarity corresponded to the formation of intermediates closely related to episulfonium ions.Transannular 1,5-hydride shift was observed for the reaction of 2,4-dinitrobensenesulfenyl dervatives with cis-cyclooctene.