SCHEDULED MAINTENANCE
Diphenylketene undergoes photocycloaddition with N-methylthiophthalimide, N-methyldithiophthalimide or xanthene-9-thione, to give a Spiro-adduct containing a thietan-2-one ring. The photoproducts from the thioimide substrates are themselves photolabile, eliminating COS to form an alkene. Diphenyl-N-(p-tolyl)ketenimine gives analogous 2-iminothietanes on irradiation with the thioimides.
J. D. Coyle, P. A. Rapley, J. Kamphuis and H. J. T. Bos, J. Chem. Soc., Perkin Trans. 1, 1985, 1957 DOI: 10.1039/P19850001957
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