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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Novel and Versatile Photosensitized Oxygenation Reaction of α-Cedrene

Author(s): Weiping Wu, Feng An, Zhengsong Geng, Ronghua Zhang and Zhiqin Jiang

Volume 10, Issue 3, 2013

Page: [223 - 227] Pages: 5

DOI: 10.2174/1570178611310030015

Price: $65

Abstract

Three types of photosensitized oxygenations of α-cedrene (CED) were investigated, including: rose bengal( RB)-sensitized photooxygenation of α-cedrene in acetonitrile produced one major stereospecific product (cedr-8- exoen-9α-ol), in which the double bond migrated to an adjacent position, this result demonstrated the singlet oxygen process; 9,10-dicyanoanthrathene (DCA) sensitized photooxygenation led to the formation of cedr-8-en-10β-ol; benzyl (BZ)-sensitized photoepoxidation furnished a stereospecific 8α,9α-cedrene epoxide, this reaction includes radical reaction mechanism.

Keywords: Sensitized photooxygenation, α-cedrene, singlet oxygen, electron transfer, regioselectivity


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