Reactivity of olefin functions of dicyclopentadiene in the Diels-Alder reaction with thionylaniline

Abstract

The sulfonamide with a benzothiazine moiety was synthesized by a Diels-Alder reaction of thionylaniline with dicyclopentadiene. The prepared adduct was oxidized to the appropriate sulfonamide with a benzothiazine moiety. The molecular and crystal structure of the sulfonamide obtained was determined by the single crystal X-ray diffraction analysis. A higher reactivity of the the olefin function of the norbornene fragment was found; and the formation of two structural isomers was revealed.