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Synthesis 1986; 1986(11): 970-972
DOI: 10.1055/s-1986-31844
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Desulfurization of Thioamides into Amides with Dinitrogen Tetroxide

Hyung Jin Kim* , Yong Hac Kim
  • *Department of Chemistry, Korea Advanced Institute of Science and Technology. Chung-yang, P.O. Box 150, Seoul, Korea
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Publikationsdatum:
20. August 2002 (online)

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Secondary and tertiary thioamides or diphenylthionocarbonate reacted readily with dinitrogen tetroxide at ca.0°C in acetonitrile to afford the corresponding amides or carbonate in good to excellent yields. The desulfurization appears to proceed via an S-nitroso intermediate by the selective electrophilic attack of nitrosonium cation on the thione sulfur atom.