SINGLET OXYGENATION OF 6-SUBSTITUTED-1,4-CYCLOOCTADIENES——A CONVENIENT SIMULTANEOUS SYNTHETIC ENTRY INTO CIS-5,8- AND TRANS-S,6-DISUBSTITUTED-1,3-CYCLOOCTADIENE CONTAINING OXYGEN DERIVATIVES

doi:10.7517/j.issn.1674-0475.1988.02.29

Imaging Science and Photochemistry ›› 1988, Vol. 6 ›› Issue (2): 29-34.DOI: 10.7517/j.issn.1674-0475.1988.02.29

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SINGLET OXYGENATION OF 6-SUBSTITUTED-1,4-CYCLOOCTADIENES——A CONVENIENT SIMULTANEOUS SYNTHETIC ENTRY INTO CIS-5,8- AND TRANS-S,6-DISUBSTITUTED-1,3-CYCLOOCTADIENE CONTAINING OXYGEN DERIVATIVES

CHEN DONG-LI, WANG DUO-YUAN, XIAO XU-LING

Institute of Photographic Chemistry, Academic Sinica, Beijing

Received:1987-01-02 Revised:1987-09-18 Online:1988-05-20 Published:1988-05-20

Abstract

Abstract: Hypocrellin A sensitized photooxygenation of 6-hydroxy-l,4-cyclooctadiene, 6-methoxy-1,4-cyclooctadiene, in methanol and 6-trimethylsiloxy-l,4-cyclooctadiene in 1,1,1-trichloroetha-ne stereoselectively got cis-5,8-disubstituted-l,3-cyclooctadiene and trans-5,6-disubstituted-l,3-cyclooctadiene respectively due to the stable conformation of starting material molecules in the ground state. Therefore a convenient simultaneous synthetic entry into cis-5,8-disubstituted-l,3-cyclooctadiene and trans-5,6-disubstituted-l,3-cydooctadiene has been introduced.

Key words: 6-substituted-1,4-cycclooctadiene, singlet oxygen, cis-5,8-disubstituted-1,3-cy-clooctadiene, trans-5,6-disubstituted-1,3-cyclooctadiene, molecular conformation

CHEN DONG-LI, WANG DUO-YUAN, XIAO XU-LING. SINGLET OXYGENATION OF 6-SUBSTITUTED-1,4-CYCLOOCTADIENES——A CONVENIENT SIMULTANEOUS SYNTHETIC ENTRY INTO CIS-5,8- AND TRANS-S,6-DISUBSTITUTED-1,3-CYCLOOCTADIENE CONTAINING OXYGEN DERIVATIVES[J]. Imaging Science and Photochemistry, 1988, 6(2): 29-34.

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SINGLET OXYGENATION OF 6-SUBSTITUTED-1,4-CYCLOOCTADIENES——A CONVENIENT SIMULTANEOUS SYNTHETIC ENTRY INTO CIS-5,8- AND TRANS-S,6-DISUBSTITUTED-1,3-CYCLOOCTADIENE CONTAINING OXYGEN DERIVATIVES

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