Hydroxylamine anion ? an effective ?-nucleophile in acyl transfer reactions

• DOI: 10.1007/bf00530586
• Publication Date: 2004-11-18T04:01:30Z
• Authors: Yu. S. Simanenko; A. F. Popov; T. M. Prokop'eva; V. A. Savelova; I. A. Belousova
• Keywords: Hydroxylamine

A kinetic-thermodynamic analysis of the behavior of hydroxylamine in reactions with acetic, toluenesulfonic, diethylphosphoric, and diethylphosphonic acid 4-nitrophenyl esters was conducted. Using the Bronsted approach, it was shown that hydroxylamine is a unique α-nucleophile, and its neutral and anionic forms are powerful acyl acceptors.