Tetrahedron

A convenient route to 1, 4-monoprotected dialdehydes, 1, 4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α, β-unsaturated aldehydes in organic …

D Dondi, I Caprioli, M Fagnoni, M Mella, A Albini

Index: Dondi, Daniele; Caprioli, Ilaria; Fagnoni, Maurizio; Mella, Mariella; Albini, Angelo Tetrahedron, 2003 , vol. 59, # 7 p. 947 - 957

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Citation Number: 24

Abstract

α, β-Unsaturated aldehydes were smoothly alkylated by radicals generated through photosensitised hydrogen abstraction of benzophenone. In this way, and by using 1, 3- dioxolane as radical precursor, monoprotected 1, 4-dialdehydes were obtained from crotonaldehyde, 2-hexenal, 4-methyl-2-pentenal and cyclohexencarboxyaldehyde in a moderate yield, and in a low yield from β-aryl-α, β-unsaturated aldehydes. With 2-alkyl-1, ...