A Remarkably Long-Lived Benzyl Carbanion

The photochemistry of ketoprofen, a widely used nonsteroidal antiinflammatory drug (NSAID) has been the subject of several studies as a result of its known phototoxicity. Photolysis of ketoprofen leads to 3-ethylbenzophenone, a process that is mediated by a short-lived carbanion. We have found that...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 6; pp. 873 - 875
Main Authors Laferrière, Marie, Sanramé, Carlos N, Scaiano, J. C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.03.2004
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACIDS
KETOPROFEN
PHOTOCHEMISTRY
ABSOLUTE RATE CONSTANTS
PHOTODECARBOXYLATION
AQUEOUS-SOLUTION
WATER
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Summary:The photochemistry of ketoprofen, a widely used nonsteroidal antiinflammatory drug (NSAID) has been the subject of several studies as a result of its known phototoxicity. Photolysis of ketoprofen leads to 3-ethylbenzophenone, a process that is mediated by a short-lived carbanion. We have found that under carefully controlled conditions in THF, the lifetime of the carbanion can be extended to several hours, thus providing a powerful tool for studying the mechanism of its formation and subsequent reactions.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol036313r