2-Lithio-1,3-dithianeand2-lithio-2-trimethylsilyl-l,3-dithianereactwithnitrilestoaffordprimaryaminoketene dithioacetals in good yields; these compounds exhibit marked ambident nucleophilicity. Use of other carboxylic acid derivatives as electrophiles normally produces acyl dithianes, however 2-lithio-2-trimethylsilyl-1,3-dithiane reacts with benzoyl cyanide to give a cyanoketene dithioacetal.
P. C. B. Page, M. B. van Niel and D. Westwood, J. Chem. Soc., Perkin Trans. 1, 1988, 269 DOI: 10.1039/P19880000269
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