Transformation of mononuclear aryl thiocarbamates to cyclic disulfides

Abstract

Thermolysis of the melt of octakis(O-thiocarbamoyl)tetra(C-phenethyl)resorcinarene in a microwave reactor afforded a cavitand, the upper rim of which was formed due to the formation of disulfide bridges between the neighboring benzene rings of the resorcinarene framework. The reaction of 2,2’-bis(carbamoylthio)-1,1’-methylenedinaphthalene with LiAlH₄ gave a tricyclic derivative, in which the naphthalene rings were bound by methylene and disulfide bridges. The structure of 2,2’-dithiinedinaphthylmethane was confirmed by single crystal X-ray diffraction analysis of this compound.