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

Necdet COŞKUN; Nevin ARIKAN

Makale detayları

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

Yazarlar:

Necdet COŞKUN | Nevin ARIKAN

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2003 Vol.27 Issue 1, pp.15-20

Belge Tipi:

Makale

Yayın Tarihi:

12/2002

Belge Dili:

Türkçe

Document ID (Org No.):

2000729658

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

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.

 

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.

Makale detayları

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

Yazarlar: Necdet COŞKUN | Nevin ARIKAN

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2003 Vol.27 Issue 1, pp.15-20

Belge Tipi: Makale

Yayın Tarihi: 12/2002

Belge Dili: Türkçe

Document ID (Org No.): 2000729658

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Necdet COŞKUN | Nevin ARIKAN

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2003 Vol.27 Issue 1, pp.15-20

Belge Tipi:

Makale

Yayın Tarihi:

12/2002

Belge Dili:

Türkçe

Document ID (Org No.):

2000729658

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527