Reactions of 2,3-Diphenylthiirene 1,1-Dioxide with Nucleophiles

Article abstract of DOI:10.1021/jo01301a013

A series of nucleophiles was allowed to react with 2,3-diphenylthiirene 1,1-dioxide (1) in dipolar aprotic solvents to produce a variety of derivatives.Fluoride ion gave diphenylacetylene and (E)-1,2-diphenylvinylsulfonyl fluoride (2);thiophenoxide gave (E)-1,2-diphenyl-2-(thiophenoxy)vinylsulfinate which gave the corresponding methyl sulfone 5 on treatment with methyl iodide.Azide ion gave a variety of products including diphenylvinyl azides 12 and 13, 2,3-diphenylazirine (14), 2,6-diphenyl-4-((E)-diphenylvinyl)-1,3,4,5-thiatriazine 1,1-dioxide (15),benzil (16), 4,5-diphenyltriazole (17), 2,4,5-triphenylimidazole (18),and (Z)-1,2-diphenyl-2-azidovinylsulfinate which gave the corresponding methyl sulfone 22 on treatment with methyl iodide.The diphenylvinyl group was removed from the new heterocycle 15 by ozonolysis followed by mild base hydrolysis to yield the thiatriazine 1,1-dioxide 20.Compound 20 undergoes thermolysis at 40 deg C to give stilbenes,and 20 also undergoes a facile base-catalyzed extrusion of sulfur dioxide to give imidazole 18.