Reactions between β-Propiolactone and Dialkyl Dimethylphosphoramidite-Ambident Character of β-Propiolactone and of Dialkyl Dimethylphosphoramidite

Abstract

Abstract The reactions between dialkyl dimethylphosphoramidite, Me2NP(OR)2, and β-propiolactone were carried out in various solvents at 80°C. Two kinds of reaction products were separated on a silica gel by elution with benzene-ethanol (4:1 v/v). The first species eluted was N,N-dimethyl-O-alkyl 2-alkoxycarbonylethylphosphoramidate, (RO)P(O)(NMe2)CH2CH2CO2R. The fraction having lower Rf value contained dialkyl 2-N,N-dimethylcarbamoylethylphosphonate, (RO)2P(O)CH2CH2CONMe2. The reaction mechanism is discussed from kinetic study.