Journal of the American Chemical Society p. 3878 - 3882 (1981)
Update date:2022-08-03
Topics:
Jarvis, Bruce B.
Nicholas, Paul E.
Midiwo, Jacob O.
Thermolyses of α-azidobenzyl phenyl sulfide (1), sulfoxide (3), and sulfone (2) proceed at markedly different rates.Sulfone 2 requires the highest temperature (> 150 deg C), whereas sulfide 1 loses nitrogen at 120 deg C with neighboring group participation by the sulfur atom to produce N-benzylidenebenzenesulfenamide 4 in 75percent yield.Sulfoxide 3 readily decomposes at 70 deg C through a radical-pair intermediate, which gives rise to a CIDNP effect in the reaction products.Kinetic data are presented supporting the suggested reaction mechanisms.
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