Selective addition of wittig reagents to bifunctionalized compounds. Condensation of 3-phenyl (2-benzothiazolyl)acrylonitrile with some phosphorus ylides

Article abstract of DOI:10.1016/S0040-4020(98)00545-6

The behaviour of the acrylonitrile 1 toward different types of phosphorus ylides such as alkoxycarbonyl- 2a,b and β-keto-alkylidene phosphoranes 2c-e as well as arylidenephosphorane 3 has been studied. The reactions take different pathways leading to unusual products, depending only on the nature of the substituents of ylides used. All reactions proceed only in the presence of a base whereby a variety of 1,3-benzothiazolyl-[1,2-x] fused compounds, e.g. 6, 16 and 18; cyclopropene- 15 and cyclopropane- 19 derivatives as well as different types of new ylides: 7, 10 and 12a,b were isolated and established on chemical and physical evidence.