ALLENES-41. THE ADDITION OF THIOLS TO ALLENYL- AND PHENYLPROPYNYLNITRILE AND THE FORMATION OF THIAZOLINES AND BENZOTHIAZOLES

Article abstract of DOI:10.1016/S0040-4020(01)88457-X

Thiols add to allenylnitriles to give unconjugated nitriles which may be isomerised to conjugated enesulphide nitriles either at high temperature (200^o) or with base.Phenylpropynenitrile gives conjugated adducts directly.Heating the conjugated adducts from aminoethanethiols at >200^o results in 5-exotrig ring closure and elimination of acetonitrile to give thiazolines and benzothiazoles.