Use of Ph3P=N-Li: Synthesis of ?,?-unsaturated nitriles from ?,?-unsaturated esters via the formation of N-(?,?-unsaturated acyl) phosphinimines

Abstract

The reaction of Ph3P=NLi with various α,β-unsaturated esters gives access to new N-(α,β-unsaturated acyl) phosphinimines, which can undergo intramolecular aza-Wittig reactions (at 65–110°C) to afford the corresponding nitriles. The structures of all new compounds were established by elementary analyses, IR, 1H-, 13C-, and 31P-NMR spectroscopy. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 49–54, 1999