13162-68-0Relevant articles and documents
Synthesis, thermal reactivity and kinetics of substituted [(benzoyl)(phenylcarbamoyl)methylene]triphenylphosphoranes and their thiocarbamoyl analogues
Aitken, R. Alan,Al-Awadi, Nouria A.,Dawson, Graham,El-Dusouqi, Osman M.E.,Farrell, Dorcas M.M.,Kaul, Kamini,Kumar, Ajith
, p. 129 - 135 (2007/10/03)
A range of 16 substituted benzoyl/arylcarbamoyl and benzoyl/ arylthiocarbamoyl stabilised ylides have been prepared. They are found under conditions of flash vacuum pyrolysis to fragment giving a benzoyl ylide and aryl isocyanate or isothiocyanate accompanied in some cases by secondary pyrolysis products. Kinetic studies show the thiocarbamoyl ylides to react consistently faster than their carbamoyl analogues and substituent effects suggest a polar cyclic transition state, which involves attack by the benzoyl oxygen on the carbamoyl/thiocarbamoyl NH. Graphical Abstract.
Cumulated Ylides, XVI. A Method for the Exchange of the OH Group in Free Carboxylic Acids by the Ylide Function
Bestmann, Hans Juergen,Schade, Gerold,Schmid, Guenter,Moenius, Thomas
, p. 2635 - 2639 (2007/10/02)
Carboxylic acids 5 react with triphenylphosphorane (4) via the intermediate 6 with formation of the phosphoranes 7, which rearrange by heating in an intramolecular acyl migration to ylides 10.By heating of 10 in the presence of an alcohol 13 the acyl ylides 11 and urethanes 14 are formed.The reaction sequence allows the replacement of the OH group in carboxylic acids by the ylide function.
