Reaction of o‐Halobenzyl Cyanides with Carbon Disulfide and Phenyl Isothiocyanate
Starting from o‐halobenzyl cyanides 1 and carbon disulfide in the presence of sodium hydride dithiolates 3 are prepared, which are not isolated. Alkylation under cooling gives ketene S, S‐acetals 4, while on heating at 100°C benzo[b]thiophenes 6 are obtained. Nitrile cyclisation yields thieno[2, 3‐b]benzothiophene 7. Reaction of 1 with phenyl isothiocyanate/sodium hydride and subsequent alkylation leads to the ketene S, N‐acetals 13 und to the thiazolidines 15.
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