Kinetics and mechanism of the anilinolysis of aryl phenyl isothiocyanophosphates in acetonitrile

• Hasi Rani Barai and
• Hai Whang Lee

Beilstein J. Org. Chem. 2013, 9, 615–620, doi:10.3762/bjoc.9.68

• Hasi Rani Barai Hai Whang Lee Department of Chemistry, Inha University, Incheon 402-751, Korea 10.3762/bjoc.9.68 Abstract Kinetic studies on the reactions of Y-aryl phenyl isothiocyanophosphates with substituted X-anilines and deuterated X-anilines were carried out in acetonitrile at 55.0 °C. The

• . Keywords: anilinolysis; cross-interaction constant; deuterium kinetic isotope effects; phosphoryl transfer reaction; reactive intermediates; Y-aryl phenyl isothiocyanophosphates; Introduction The nucleophilic substitution reactions of tetracoordinate phosphorus have been studied extensively

• transition state (TS). To extend the kinetic studies on the phosphoryl transfer reactions, the reactions of Y-aryl phenyl isothiocyanophosphates (1a–e) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) have been investigated kinetically in acetonitrile (MeCN) at 55.0 ± 0.1 °C (Scheme 1