REDUCTIVE DEIMINATION OF SULFOXIMIDES AND SULFIMIDES WITH P-TOLUENESULFONYL NITRITE AND T-BUTYL THIONITRATE1 |
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Authors: | Shigeru Oae Kazuyuki Iida Toshikazu Takata |
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Affiliation: | Department of Chemistry , The University of Tsukuba , Sakura, Ibaraki, 305, Japan |
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Abstract: | Abstract Reduction of sulfimides and sulfoximides with p-toluenesulfonyl nitrite, a new nitrosating agent, gave nearly quantitatively the corresponding deimination products, sulfides and sulfoxides, respectively. In the reaction of dialkyl and aryl alkyl sulfoximides with t-butyl thionitrate, N-t-butylthiosulfoximides were obtained besides the usual deimination products, although diaryl sulfoximides were readily deiminated to the corresponding sulfoxides in good yields in the same treatment. t-Butyl thionitrate was also found to deiminate diphenyl sulfimide to give diphenyl sulfide in good yield. Sulfoximides reacted sluggishly with t-butyl thionitrite, however, eventually affording a small amount of sulfoxides. |
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Keywords: | N-(2-cyano-1-methyl-etheny1)-O,O-diphenyl-amido-phosphate N-(2-cyano-1-methyl-ethenyl)-O,O-diphenyl-amido-thiophosphate N-(diphenoxy-thiophosphoryl)-3-amino-crotonitrile N-(O,O-diphenyl-thiophosphatyl)-3-amino-crotonitrile acetonitrile diphenoxyphosphorylchloride diphenoxythiophosphorylchloride x-ray structure analysis hydrogen bonds |
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