Syntheses of α,β-Unsaturated Carbonyl Compounds from the Reactions of Monosubstituted Ozonides with Stable Phosphonium Ylides

Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-α,β-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-α,β-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed.