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 : 16 | Download : 11

Publication Date : 9999-12-31

Article Type : Makaleler

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-(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. Full text: pdf Other articles published in the same issue: Turk. J. Chem., vol.27, iss.1.