Unusual regiochemistry in a beckmann-like rearrangement of camphor. α-Camphidone via methylene migration. |
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Authors: | Grant R Krow Steven Szczepanski |
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Institution: | Department of Chemistry, Temple University, Phila., PA 19122 U.S.A. |
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Abstract: | Reaction of camphor with hydroxylamine-O-sulfonic acid affords the nitrogen insertion product α-camphidone by migration of the methylene group rather than the bridgehead. Since Beckmann rearrangements of trigonal oximes afford bridgehead cleavage products with camphor, an alternative synchronous rearrangement of a tetrahedral intermediate is proposed for this Beckmann-like reaction. |
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