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Cycloaddition Reactions of Heterocumulenes, XXIX. - Reactions of Thioketenes with Isocyanates
Schaumann, Ernst,Moeller, Marianne,Adiwidjaja, Gunadi
, p. 689 - 700 (2007/10/02)
The cycloaddition of thioketenes 1a-f to isocyanates 2a-f yields 4-thioxo-2-azetidinones 3 as main products, which may isomerize to 4-imino-2-thietanones 5.In competing reactions, 2,4-azetidinediones 8, N-sulfonylamides 9, and 3H-1,2,4-dithiazoles 15 are formed.Thioketenes 1 react with chlorosulfonyl isocyanate (20b) to give N-unsubstituted 4-thioxo-2-azetidinones 22.Depending on the thioketene 1 and the reaction conditions, compounds 23-26 also result.The consitutions of 15b and 23a were determined by X-ray structural analyses.
