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Effects of oxygenated substituents on the [4+2] cycloaddition of singlet oxygen in the photooxygenation of water-soluble naphthyl ethers

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
41
Issue
26
Identifiers
DOI: 10.1016/s0040-4039(00)00793-0

Abstract

Abstract Water-soluble ethers 2 and 5 undergo [4+2] cycloaddition of singlet oxygen to afford endoperoxides. Compound 2 is extremely reactive ( k r+ k q=2.0×10 8 M −1/s −1 in D 2O) due to the mesomeric interactions between oxygen and the naphthalene ring. However, the unstable endoperoxide was immediately and quantitatively decomposed into the aldehyde ester 6. When a methylene linker separates the oxygen from the aromatic core ( 5), photooxidation leads to a mixture of 1,4 and 5,8-endoperoxides.

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