Document Detail


Electrophilic reactivities of azodicarboxylates.
MedLine Citation:
PMID:  20836096     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
The kinetics of the reactions of the azodicarboxylates 1 with the enamines 2 have been studied in CH(3) CN at 20 °C. The reactions follow a second-order rate law and can be described by the linear free energy relationship log k(2) (20 °C)=s(N+E) (E=electrophilicity parameter, N=nucleophilicity parameter, and s=nucleophile-specific slope parameter). With E parameters from -12.2 to -8.9, the electrophilic reactivities of 1 turned out to be comparable to those of α,β-unsaturated iminium ions, amino-substituted benzhydrylium ions, and ordinary Michael acceptors. While the E parameters of the azodicarboxylates 1 determined in this work also hold for their reactions with triarylphosphines, they cannot be used for estimating rate constants for their reactions with amines. Comparison of experimental and calculated rate constants for cycloadditions and ene reactions of azodicarboxylates provides information on the concertedness of these reactions.
Authors:
Tanja Kanzian; Herbert Mayr
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Publication Detail:
Type:  Journal Article     Date:  2010-09-10
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  16     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2012-10-05     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  11670-7     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377 München (Germany), Fax: (+49) 89-2180-77717.
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