2-Chloro-2-phenyl-2-(p-tolylthio)-1,3-diorgano-1,3,2λ5-diazaphosphetidin-4-ones

The reaction of N,N'-dimethyl-N,N'-bis(trimethylsilyl)urea (1) or N-methyl-N'-phenyl-N,N'-bis(trimethylsilyl)urea (2) with p-toluenesulfenyl chloride furnished N,N'-dimethyl-N-(p-tolylthio)-N'-(trimethylsilyl)urea (3) and N-methyl-N'-phenyl-N'-(p-tolylthio)-N-(trimethylsilyl)urea (4), respectively. The reaction of PhPCl 2 with compounds 3 and 4 resulted in the formation of the title compounds 6 and 7. Their identity and structure were established by 1 H-, 13 C- and 31 P-NMR spectroscopy and by a single-crystal X-ray structure analysis in the case of 7, in which the geometry at phosphorus is that of a distorted trigonal bipyramid with the axial P-N bond significantly longer than in similar phosphoranes. The mechanism of formation of phosphorane 6 and 7 is discussed

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