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Search for a nonelectrocyclic cyclization of nitrosostyrene: Rearrangements of Michael adducts from DMAD and alpha-dialkylamino oximes

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Coşkun, Necdet
Arıkan, Nevin

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TÜBİTAK

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The aza-Claisen rearrangement product of the Michael adducts 2 from alpha-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.

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Chemistry, Engineering, N-oxides

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Coşkun, N. ve Arıkan, N. (2003). “Search for a nonelectrocyclic cyclization of nitrosostyrene: Rearrangements of Michael adducts from DMAD and alpha-dialkylamino oximes”. Turkish Journal of Chemistry, 27(1), 15-20.

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