Moderate generation of sulfenylnitrenes from novel N-sulfenylsulfodiimides

Abstract

N-Sulfenylated sulfodiimides were first prepared by the reaction of S, S-diphenyl- N-tosylsulfodiimide with arenesulfenyl chlorides under the basic conditions. Thermolysis of S, S-diphenyl- N-(2-nitrophenylsulfenyl)- and S, S-diphenyl- N-(2,4-dinitrophenylsulfenyl)sulfodiimides in the presence of olefins proceeded at 50–80 °C to give the corresponding deiminated S, S-diphenyl- N-tosylsulfimide and N-sulfenylaziridines in very good yields. 2,4-Dinitrophenyl-sulfenylnitrene was trapped by trans- and cis-1-phenylpropenes stereospecifically. The thermolysis temperature of the N-sulfenylsulfodiimides was found to be lower than N-sulfenylsulfoximide and higher than N-sulfenyliminosulfonium salt and very effective to trap the sulfenylnitrene to give the N-sulfenylaziridines in very good yields.