Universität zu Köln

Rajachan, Oue-artom, Paul, Mathias, Yatham, Veera Reddy ORCID: 0000-0002-3967-5342, Neudoerfl, Joerg-M., Kanokmedhakul, Kwanjai, Kanokmedhakul, Somdej and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2015). N-Heterocyclic carbene catalyzed tail-to-tail oligomerization of N,N-dimethylacrylamide (DMAA) and the search for the Stetter reaction of DMAA with benzaldehyde. Tetrahedron Lett., 56 (47). S. 6537 - 6541. OXFORD: PERGAMON-ELSEVIER SCIENCE LTD. ISSN 0040-4039

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Abstract

The tail-to-tail oligomerization of N,N-dimethylacrylamide catalyzed by N-heterocyclic carbenes (NHCs) was investigated, giving the dimerization and trimerization products in a moderate combined yield. Reaction intermediates involved in the new oligomerization have been observed by NMR and ESI-MS. We showed the first NHC-catalyzed cross coupling of methyl methacrylate and N,N-dimethylaciylamide, and the reaction of benzaldehyde/benzoin with N,N-dimethylacrylamide. (C) 2015 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Rajachan, Oue-artom UNSPECIFIED UNSPECIFIED UNSPECIFIED Paul, Mathias UNSPECIFIED UNSPECIFIED UNSPECIFIED Yatham, Veera Reddy UNSPECIFIED orcid.org/0000-0002-3967-5342 UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Kanokmedhakul, Kwanjai UNSPECIFIED UNSPECIFIED UNSPECIFIED Kanokmedhakul, Somdej UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-386769
DOI:	10.1016/j.tetlet.2015.09.104
Journal or Publication Title:	Tetrahedron Lett.
Volume:	56
Number:	47
Page Range:	S. 6537 - 6541
Date:	2015
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Place of Publication:	OXFORD
ISSN:	0040-4039
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language THIAMINE ACTION; UMPOLUNG; DIMERIZATION; MECHANISM; INTERMEDIATE; GENERATION Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/38676