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

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

Source and publish data:

Tetrahedron Letters p. 4593 - 4596 (1980)

Update date:2022-08-05

Topics:

Authors:

Krow, Grant R.

Szczepanski, Steven

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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.

Full text of DOI:10.1016/0040-4039(80)80082-7

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