BECKMANN FRAGMENTATION VERSUS BECKMANN REARRANGEMENT IN DEHYDRONORCAMPHOR DERIVATIVES

DOI: 10.1016/S0040-4039(00)99316-X

Source and publish data:

Tetrahedron Letters p. 4041 - 4044 (1989)

Update date:2022-08-06

Topics:

Authors:

VerHaeghe, Daniel G.

Weber, Gregory S.

Pappalardo, Paul A.

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Article abstract of DOI:10.1016/S0040-4039(00)99316-X

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.

Full text of DOI:10.1016/S0040-4039(00)99316-X

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