Unusual regiochemistry in a beckmann-like rearrangement of camphor. α-Camphidone via methylene migration.

Article abstract of DOI:10.1016/0040-4039(80)80082-7

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.