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Dergiler / Turkish Journal of Chemistry / 2003 / Cilt: 27 - Sayı: 1

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

Necdet COŞKUN
Nevin ARIKAN
Sayfa
15–20
Yayın Tarihi
2022-11-04
DOI
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Compounds 9 isomerized to 8 on heating in acetonitrile.

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Amaç & Hipotez: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.
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Temel Bulgular & Veri:The fragmentation was assumed to proceed through an unstable 4H-1,2-oxazete 6.
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Sonuç & Katkı:Compounds 9 isomerized to 8 on heating in acetonitrile.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

Abstract

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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Bu Makaleye Atıf Yap

COŞKUN, N., ARIKAN, N. (2022). Search for a nonelectrocyclic cyclization of nitrosostyrene: Rearrangements of Michael adducts from DMAD and $alpha$-dialkylamino oximes. Turkish Journal of Chemistry, Cilt: 27 - Sayı: 1, 15–20. https://ajindex.com/articles/602257

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Kaynakça (19)

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