Reactions of Aryliminotriphenylphosphoranes with Sulfenes

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概要

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• Aryliminotriphenylphosphoranes reacted with methanesulfonyl, ethanesulfonyl and α-toluenesulfonyl chlorides in the presence of triethylamine to give 1 : 2 adducts [α-(<I>N</I>-alkanesulfonyl-<I>N</I>-arylsulfamoyl)alkylidenephosphoranes] and the decomposition products, instead of 1 : 1 adducts [α-(<I>N</I>-arylsulfamoyl)alkylidenephosphoranes). They were obtained under ice-cooling, the structure being of betaine type. In the case of methanesulfonyl chloride, isomeric 1 : 2 adduct [α-(<I>N</I>-arylsulfamoyl)methanesulfonylmethylenephosphorane] was also obtained. 2-Propanesulfonyl chloride gave <I>N</I>-triphenylphosphonio-<I>N</I>-arylsulfamate instead of expected adduct. In the absence of triethylamine, α-(<I>N</I>-arylsulfamoyl) alkyltriphenylphosphonium chlorides were obtained in good yields. Possible mechanisms of these reactions have been discussed.

• 公益社団法人 日本化学会の論文

著者

• Kawashima Takayuki

  Department Of Chemistry Faculty Of Science The University Of Tokyo

• Inamoto Naoki

  Department of Chemistry and Research Centre for Spectrochemistry, Faculty of Science, The University of Tokyo

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