Pyridinolyses of O-Propyl and O-Isopropyl Phenyl Phosphonochloridothioates in Acetonitrile

摘要

Continuing the kinetic studies on the pyridinolyses of the phosphonochloridothioates, the nucleophilic substitution reactions of O-propyl (4) and O-isopropyl (5) phenyl phosphonochloridothioates with X-pyridines have been carried out kinetically in acetonitrile (MeCN) at 35.0 ± 0.1 °C (Scheme 1). The kinetic results of the present work are compared with those of the pydidinolyses of Y-O-aryl methyl [1; Me(YC6H4O)P(=S)Cl], O-methyl phenyl [2; Ph(MeO)P(=S)Cl], O-ethyl phenyl [3; Ph(EtO)P(=S)Cl], Y-O-aryl phenyl [6; Ph(YC6H40)P(=S)Cl] and Y-S-aryl phenyl [7; Ph(YC6H4S)P(=S)Cl] phosphonochloridothioates, based on the reactivities, selectivity parameters, free energy correlations and reaction mechanisms.