Abstract
The reactions between S-nitrosothiols and phosphite esters, including P(OPh)(3), P(OBn)(3), and P(OEt)(3), were studied. Two different conjugated adducts, thiophosphoramidates and phosphorothioates, were formed, depending on the structures of the S-nitrosothiol substrate (e.g., primary vs tertiary). These reactions proceeded under mild conditions, and the reaction mechanisms were studied using experiments and calculations.