136664-69-2Relevant academic research and scientific papers
Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates
Wang, Gao,Yu, Qing-Ying,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information, p. 6230 - 6232 (2013/10/22)
An efficient method to generate N-P bonds directly from N-H and P-H bonds is described. Various arylamines and dialkylphosphites were directly oxidized to the corresponding N-arylphosphoramidates at room temperature in moderate to good yields by using an inexpensive catalyst-oxidant (CuBr/air) system.
Kinetics and mechanism of the anilinolysis of dibutyl chlorophosphate in acetonitrile
Hoque, Md. Ehtesham Ul,Lee, Hai Whang
experimental part, p. 663 - 669 (2012/05/19)
The nucleophilic substitution reactions of dibutyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 °C. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.86-0.97) with the strongly basic anilines while primary normal (kH/kD = 1.04-1.10) with the weakly basic anilines. The DKIEs, steric effects of the two ligands, activation parameters, cross-interaction constants, variation trends of the kH/kD values with X, and mechanism are discussed for the anilinolyses of the nine (R1O)(R2O)P(=O)Cl-type chlorophosphates. A concerted mechanism is proposed with a backside nucleophilic attack transition state for the strongly basic anilines and with a frontside attack involving a hydrogen-bonded four-center-type transition state for the weakly basic anilines on the basis of the magnitudes, secondary inverse and primary normal, and variation trends of the kH/kD values with X.
