Zur Reaktion von o-Halogenbenzylcyaniden mit Schwefelkohlenstoff und Phenylisothiocyanat

✍ Scribed by Dr. W.-D. Rudorf; Dipl. chem. M. A. Schierhorn; Prof. Dr. M. Augustin

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: English
• Weight: 366 KB
• Volume: 321
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19793210618

✦ Synopsis

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.