STUDIES ON ORGANOPHOSPHORUS COMPOUNDS .96. NUCLEOPHILICITY OF THE ISOCYANO CARBON-ATOM IN DIETHYL ISOCYANOMETHYLPHOSPHONATE - FIRST GENERATION OF A PHOSPHORYLATED NITRILE YLIDE AND NEW SYNTHESES OF PYRROLINEPHOSPHONATES AND PYRROLEPHOSPHONATES
Ws. Huang et al., STUDIES ON ORGANOPHOSPHORUS COMPOUNDS .96. NUCLEOPHILICITY OF THE ISOCYANO CARBON-ATOM IN DIETHYL ISOCYANOMETHYLPHOSPHONATE - FIRST GENERATION OF A PHOSPHORYLATED NITRILE YLIDE AND NEW SYNTHESES OF PYRROLINEPHOSPHONATES AND PYRROLEPHOSPHONATES, Journal of the Chemical Society. Perkin transactions. I, (15), 1996, pp. 1893-1895
Reactions of acyl chlorides with diethyl isocyanomethylphosphonate aff
ord alpha-ketoimidoyl chlorides which, when treated with triethylamine
, provide a new class of nitrile ylides. These species react in situ w
ith alkenes by a 1,3-dipolar cycloaddition mechanism to give phosphory
l pyrrolines or pyrroles.