NMR study and AIM analysis for assignment of the two Z- and E-isomers in phosphorane containing a 2-thiazoline-2-thiol

AbstractTriphenylphosphine reacts with dialkyl acetylenedicarboxylates in the presence of a SH-heterocyclic compound such as 2-thiazoline-2-thiol to generate stable phosphorus ylides. These stable ylides exist in solution as a mixture of the two geometrical isomers as a result of restricted rotation around the carbon–carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group. In the recent work, NMR study and the assignment of more stable Z- or E-isomers as the major form were investigated by using natural population analysis (NPA)