Search for a Nonelectrocyclic Cyclization of Nitrosostyrene: Rearrangements of Michael Adducts from DMAD and a-Dialkylamino Oximes

Authors : Necdet COŞKUN, Nevin ARIKAN

Pages : 15-20

View : 17 | Download : 8

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The aza-Claisen rearrangement product of the Michael adducts 2 from a-dialkylaminoacetophenone oximes and DMAD underwent fragmentation to give dialkylaminomaleate, and benzonitrile at reflux in acetonitrile. The fragmentation was assumed to proceed through an unstable 4H-1,2-oxazete 6. The same reaction performed at room temperature, in addition to the nitrile and maleate, gave the corresponding 2-insert ignore into journalissuearticles values(2-dialkylamino-1-phenylethylideneaminooxy);-but-2- enedioic acid dimethyl esters 8 and 9. Compounds 9 isomerized to 8 on heating in acetonitrile.
Keywords : Turk J Chem, 27, 2003, 15 20 Turk J Chem, vol 27, iss 1