Tetrahedron p. 13765 - 13774 (1994)
Update date:2022-08-06
Topics:
Castells
Lopez-Calahorra
Yu
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.
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