Beckmann Rearrangement of 3-carboxybicyclo[3.3.1]nonane and [3.2.1]octane Oximes

Marian Gorichko, Andriy Bulochnikov, Olga Ryzhenko


Regiospecific Beckmann rearrangement of substituted 2-hydroximinonorbornanone carboxylic acids has been investigated. Selective formation of new functionalized 10-oxo-9-azabicyclo[3.3.2]decanes and 7-oxo-6-azabicyclo[3.2.2]nonanes in good yield has been demonstrated. Presence of neighboring carboxylic group allows conducting of Beckmann rearrangement of strained bicyclic compounds


Beckmann rearrangement, oxime, bicyclo[3.3.1]nonane, bicyclo[3.2.1]octane, lactam

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