BECKMANN FRAGMENTATION VERSUS BECKMANN REARRANGEMENT IN DEHYDRONORCAMPHOR DERIVATIVES
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.
VerHaeghe, Daniel G.,Weber, Gregory S.,Pappalardo, Paul A.
p. 4041 - 4044
(2007/10/02)
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