83345-82-8Relevant academic research and scientific papers
Thermal Reaction of Phenylnitrene with Sulfides
Benati, Luisa,Grossi, Mario,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 763 - 765 (1982)
Thermolysis of phenyl azide in the presence of sulfides bearing α-hydrogen atoms leads to the formation of significant amounts of 2-substituted anilines, presumably by Sommelet-Hauser type rearrangement of the intermediate N-phenylsulfimides.
N-Phehylsulphimide Formation and Rearrangement in the Thermal Reaction of Phenylnitrene with Sulphides
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 771 - 776 (2007/10/02)
Thermal reaction of phenyl azide (1) with thioanisole (2a), dimethyl sulphide (2b), and tetrahydrothiophen (2c) leads to the formation of 2-substituted anilines (3a-c) by Sommelet-Hauser rearrangement of the intermediate N-phenylsulphimides arising from phenylnitrene attack at the sulphur atom of (2a-c).Reaction with ethyl phenyl sulphide (2d) gives benzenesulphenanilide (8) and ethylene by cycloelimination of the resulting N-phenylsulphimide.Reaction with acyclic benzylic sulphides (2e-g) apparently leads only to the insertion products of phenylnitrene into benzylic C-H bond, presumably through Stevens rearrangement of the intermediate sulphimides, whereas Sommelet-Hauser rearrangement appears to compete favourably with Stevens rearrangement in the sulphimide resulting from reaction of phenylnitrene with the cyclic benzylic sulphide (2h).
