Tetrahedron

Syntheses of α, β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides

YS Hon, L Lu, RC Chang, SW Lin, PP Sun, CF Lee

Index: Hon, Yung-Son; Lu, Ling; Chang, Rong-Chi; Lin, Sheng-Wun; Sun, Pei-Pei; Lee, Chia-Fu Tetrahedron, 2000 , vol. 56, # 47 p. 9269 - 9279

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Citation Number: 38

Abstract

Ozonides derived from terminal alkenes reacted with 1.3 molequiv. 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 ...