期刊
TETRAHEDRON LETTERS
卷 41, 期 26, 页码 5063-5067出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)00793-0
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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 x 10(8) M-1/s(-1) in D2O) 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. (C) 2000 Elsevier Science Ltd. All rights reserved.
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