An Unusual Radical Smiles Rearrangement

Radicals derived from N-(α-xanthyl)acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced...

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Bibliographic Details
Published inOrganic letters Vol. 7; no. 17; pp. 3817 - 3820
Main Authors Bacqué, Eric, El Qacemi, Myriem, Zard, Samir Z
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.08.2005
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
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Summary:Radicals derived from N-(α-xanthyl)acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol051568l