Tetrahedron Letters p. 4041 - 4044 (1989)
Update date:2022-08-06
Topics:
VerHaeghe, Daniel G.
Weber, Gregory S.
Pappalardo, Paul A.
Attempted Beckmann rearrangement of dehydronorcamphor oxime resulted in Beckmann fragmentation and dimerization of the intermediate cyanomethylcyclopenta-1,3-diene isomers.The dienes can be trapped by N-phenylmaleimide to yield two isomeric crystalline adducts.When the olefin in dehydronorcamphor oxime is effectively blocked, Beckmann rearrangement takes place to provide stereochemically pure bicyclic lactam.
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