Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)methylene]triphenylphosphoranes and their thiocarbamoyl analogues

✍ Scribed by R. Alan Aitken; Nouria A. Al-Awadi; Osman M. E. El-Dusouqui; Dorcas M. M. Farrell; Ajith Kumar

• Book ID: 102446271
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 116 KB
• Volume: 38
• Category: Article
• ISSN: 0538-8066
• DOI: 10.1002/kin.20170

✦ Synopsis

Abstract

A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph~3~PO or Ph~3~PS. Kinetic study of the gas‐phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40–65 times more rapidly than their carbamoyl analogues 2. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 38: 496–502, 2006