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Synthesis 1985; 1985(10): 956-958
DOI: 10.1055/s-1985-31400
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Thermal Rearrangements of N-Aryl-1-alkynesulphenamides into Indoline-2-thiones

J. -B. Baudin* , M. Bekhazi, S. A. Julia, O. Ruel, R. L. P. De Jong, L. Brandsma
  • *E. R. 12 C. N. R. S., Laboratoire de Chimie, Ecole Normale Supérieure, 24 rue Lhomond, F-75239 Paris Cedex 05, France
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Publication Date:
27 September 2002 (online)

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Reaction of bromomagnesium benzenamides with 1-alkynyl thiocyanates affords the title sulphenamides. On heating in benzene, these sulphenamides undergo [3.3]-sigmatropic rearrangements followed by cyclisation of the intermediate thioketenes yielding indoline-2-thiones.