The higher homologues of the well-studied alkoxycarbonylmethylenetriphenylarsonium(1) ylide (3, R=H) can be easily obtained through the sequence: a). preparation of alkyl 2-trifloxyalkanoates (1); b), reaction between these trifloxyderivatives and triphenylphosphine to give 1-alkoxycarbonylalkyltriphenylarsonium triflates (2); and c), basic treatment of the triphenylarsonium triflates (2) with alumina-supported potassium fluoride to give 1-alkoxycarbonylalkyledenetriphenylarsonium ylides (3). These higher homologues of(3, R=H) react with aromatic aldehydes in good to excellent yields. and give rise to synthetically interesting ''coupling'' and cyclopropanation reactions.
A General Method for the Rapid High Yield Preparation of Pure Arsonium Salts. Preparation Of (3-Alkoxy-Carbonyl-2-Oxopropyl)Triphenylarsonium Bromides
作者:Cornelis M. Moorhoff
DOI:10.1080/00397919808004872
日期:1998.8
Abstract An easy, rapid method for the preparation of arsonium salts of high yield and purity, by heating an alkyl halide and triphenylarsine as a melt at about 80°C, is described.