Unusual effect of a remote SO2 group on the reactivity of the double bond in unsaturated cyclic sulphones towards ethoxycarbonylnitrene

Abstract

Except in a two-phase system and contrary to expectation, ethoxycarbonylnitrene when generated from Lwowski's reagent by α-elimination does not add to the unsaturated cyclic sulphones (1)–(10) owing to the presence of orbital interactions (through bonds and through space)between the SO₂ group and the double bond, as evidenced by u.v.–photoelectron spectrosocopy.