Beilstein J. Org. Chem.2013,9, 615–620, doi:10.3762/bjoc.9.68
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Keywords: anilinolysis; cross-interactionconstant; 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
increases with a more electron-withdrawing substituent.
The cross-interactionconstant (CIC) is defined based on the substituent effects of the nucleophiles, substrates and/or leaving groups on the reaction rates [3][4][5]. In the present work, the CIC (ρXY) between substituents X and Y in the nucleophiles
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Graphical Abstract
Scheme 1:
Reactions of Y-aryl phenyl isothiocyanophosphates (1a–e) with XC6H4NH2(D)2 in MeCN at 55.0 °C.