Thermolysis of. alpha.-azido sulfides, sulfoxides, and sulfones: dependence of mechanism on oxidation state of sulfur

BB Jarvis, PE Nicholas, JO Midiwo

Index: Jarvis, Bruce B.; Nicholas, Paul E.; Midiwo, Jacob O. Journal of the American Chemical Society, 1981 , vol. 103, # 13 p. 3878 - 3882

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Citation Number: 11

Abstract

Abstract: Thermolyses of a-azidobenzyl phenyl sulfide (l), sulfoxide (3), and sulfone (2) proceed at markedly different rates. Sulfone 2 requires the highest temperature (> 150" C), whereas sulfide 1 loses nitrogen at 120 OC with neighboring group participation by the sulfur atom to produce N-benzylidenebenzenesulfenamide 4 in 75% yield. Sulfoxide 3 readily decomposes at 70 OC through a radical-pair intermediate, which gives rise to a ...