An unusual radical Smiles rearrangement |
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Authors: | Bacqué Eric El Qacemi Myriem Zard Samir Z |
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Affiliation: | Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau, France. |
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Abstract: | Radicals derived from N-(alpha-xanthyl)acetanilides or N-(alpha-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. [reaction: see text] |
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