Universität zu Köln

Knappke, Christiane E. I., Arduengo, Anthony J., III, Jiao, Haijun, Neudoerfl, Joerg-Martin and Jacobi von Wangelin, Axel (2011). On the Dual Role of N-Heterocyclic Carbenes as Bases and Nucleophiles in Reactions with Organic Halides. Synthesis (23). S. 3784 - 3796. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-210X

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Abstract

The synthetic consequences of different basicities, nucleophilicities, and sterics of N-heterocyclic carbenes have been studied in reactions of imidazolin-2-ylidenes with organic halides. Highly nucleophilic and less basic carbenes cleanly gave alkylideneimidazolines, the deoxy analogues of Breslow-type intermediates. More basic NHCs engaged in unwanted deprotonation or dehydrohalogenation reactions.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Knappke, Christiane E. I. UNSPECIFIED UNSPECIFIED UNSPECIFIED Arduengo, Anthony J., III UNSPECIFIED UNSPECIFIED UNSPECIFIED Jiao, Haijun UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Jacobi von Wangelin, Axel UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-484970
DOI:	10.1055/s-0031-1289593
Journal or Publication Title:	Synthesis
Number:	23
Page Range:	S. 3784 - 3796
Date:	2011
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-210X
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language DIELS-ALDER REACTION; IMIDAZOLE DERIVATIVES; STABLE CARBENES; OLEFIN; SALTS; COORDINATION; UMPOLUNG; BASICITY; 2-ALKYLIDENEIMIDAZOLIDINES; ALKYLATION Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/48497