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
Full Text: HTML
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 ...
Related Articles:
[Gilman; Morris Journal of the American Chemical Society, 1926 , vol. 48, p. 2403]
[Gilman; Morris Journal of the American Chemical Society, 1926 , vol. 48, p. 2403]
[Gilman; Morris Journal of the American Chemical Society, 1926 , vol. 48, p. 2403]
[Gilman; Morris Journal of the American Chemical Society, 1926 , vol. 48, p. 2403]
[Oh, Hyuck Keun; Koh, Han Joong; Lee, Ikchoon Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991 , # 12 p. 1981 - 1984]