Synthesis of Nitriles via the Ylide Anion of Sodium Cyanotriphenylphosphoranylidenemethanide

A convenient access to nitriles having a variety of extremely different structures is provided by the ylide anion 1, which is isolable as the sodium salt. By reaction with alkyl halides RX, 1 can be converted into cyclic α,β-unsatu-rated nitriles such as 2; the “dienyl cyanides” 3 and alkynyl cyanides RCCCN are obtainable from 1 by reaction with aldehydes RCHO and esters RCOOR', respectively.