Tetrahedron

Sensitized photo-oxygenation of acyclic conjugated dienes

M Matsumoto, S Dobashi, K Kuroda, K Kondo

Index: Matsumoto, Masakatsu; Dobashi, Satoshi; Kuroda, Keiko; Kondo, Kiyosi Tetrahedron, 1985 , vol. 41, # 11 p. 2147 - 2154

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Citation Number: 53

Abstract

Sensitized photo-oxygenation of a wide variety of acyclic 1, 3-dienes was investigated. The 1, 4-cycloaddition of singlet oxygen to acyclic conjugated dienes was closely related to the thermal Diels-Alder reaction in stereospecificity, and steric and electronic effects of substituents. Reactivity order of singlet oxygen toward conjugated dienes and isolated C—C double bonds was exhibited as follows: trisubstituted mono-olefins> 2-substituted 1, 3- ...