NMR Investigation of the Reaction of 1,1-Diarylethylenes with Seleninyl Chloride and Diselenium Dichloride

The reaction of 1, 1-diarylethylenes with seleninyl chloride (SeOCl2) and with diselenium dichloride (Se2Cl2) to yield benzoselenopheno [2,3-b] benzoselenophens was investigated by NMR. Several reaction intermediates have been tentatively identified in the reaction of 1, 1-diphenylethylene, but its para-substituted derivatives yielded no additional mechanistic information. The reaction of 1, 1-diphenylethylene with thionyl chloride was also studied by NMR. Both the SeOCl2 and the SOCl2 reactions occur through analogous primary addition compounds.