162213-19-6Relevant articles and documents
1-alkoxycarbonylalkylidenetriphenylarsoranes: Preparation and reactions
Castells,Lopez-Calahorra,Yu
, p. 13765 - 13774 (1994)
The higher homologues of the well-studied alkoxycarbonylmethylenetriphenylarsonium 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.