Single Electron Transfer Induced Photoaddition Reactions of Silyl Enol Ether to N-Methylphthalimide

Photochemical reactions of N-methylphthalimide with silyl enol ethers have been explored. Irradiations of phthalimide (1) and cyclic silyl enol ethers (5a-b) are observed to promote formation of photoreduced phthalimides and photoaddition products by sequential SET-desilylation pathways. The photore...

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Bibliographic Details
Published inBulletin of the Korean Chemical Society Vol. 28; no. 4; pp. 629 - 634
Main Authors Oh, Sun-Wha, Kim, Jin-Young, Cho, Dae-Won, Choi, Jung-Hei, Yoon, Ung-Chan
Format Journal Article
LanguageKorean
Published 2007
Subjects
Silyl enol ethers
Single electron transfer
Photocycloaddition
Oxetane
N-Methylphthalimide
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Summary:Photochemical reactions of N-methylphthalimide with silyl enol ethers have been explored. Irradiations of phthalimide (1) and cyclic silyl enol ethers (5a-b) are observed to promote formation of photoreduced phthalimides and photoaddition products by sequential SET-desilylation pathways. The photoreaction of phthalimide (1) and acyclic silyl enol ethers (5c-d) leads to produce oxetanes which arise by competitive single electron transfer (SET) and classical 2+2 photocycloaddition (Parteno-Buchi reaction) pathways.
Bibliography:KISTI1.1003/JNL.JAKO200702727052537
ISSN:0253-2964
1229-5949