Regioselective ?- and ?-Addition to Alkyl Propiolates: Experimental and Theoretical Study

Abstract

In this paper, two different regioselectivity in reaction of nucleophiles with alkyl propiolates were reported. In present experiments, the reaction of NH and OH containing acids with alkyl propiolates in presence of triphenyl phosphine were studied. After determining final structure of products, it was shown that the NH acids added to the α-position and OH acids added to the β-position of alkyl propiolates. These experimentals results have been confirmed by theoretical study using ab initio and denisty functional methods.