Singlet oxygenation of 4-(4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran-5-yl)-2-pyridone: non-stereospecific 1,4-addition of singlet oxygen to a 1,3-diene system and thermal rearrangement of the resulting 1,4-endoperoxides to stable 1,2-dioxetanes

Singlet oxygen adds easily to a 1,3-diene 1, whose E-Z double bond isomerization can not take place, to give a mixture of stereoisomeric 1,4-endoperoxides 2 which rearranges into a thermally stable 1,2-dioxetane 5 selectively on heating in benzene.

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 10; pp. 821 - 822
Main Authors Matsumoto, M, Nasu, S, Takeda, M, Murakami, H, Watanabe, N
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.05.2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DECOMPOSITION
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Summary:Singlet oxygen adds easily to a 1,3-diene 1, whose E-Z double bond isomerization can not take place, to give a mixture of stereoisomeric 1,4-endoperoxides 2 which rearranges into a thermally stable 1,2-dioxetane 5 selectively on heating in benzene.
ISSN:1359-7345
1364-548X
DOI:10.1039/b002161j