131292-25-6Relevant articles and documents
Flash Vacuum Pyrolysis of Stabilised Phosphorus Ylides. Part 2. Two-step Conversion of Acid Chlorides into Acetylenic Esters and Terminal Alkynes
Aitken, R. Alan,Horsburg, Caroline E. R.,McCreadie, J. Graeme,Seth, Shirley
, p. 1727 - 1732 (2007/10/02)
The known thermal extrusion of Ph3PO from α-acyl-α-ethoxycarbonyl ylides 1 to give acetylenic esters 2 can be accomplished in excellent yield by using flash vacuum (FVP) at 500 deg C.Upon rasing the furnace temperature to 750 deg C, this reaction is accompanied by unexpected loss of the ethoxycarbonyl group to give the terminal alkynes 7 in moderate yield.A mechanism is proposed for this reaction based on isotopic labelling studies.Ten new examples of ylides 1 have been prepared for the first time.