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The aza-Morita-Baylis-Hillman reaction: a mechanistic and kinetic study.

The aza-Morita-Baylis-Hillman reaction: a mechanistic and kinetic study.

Authors :
Lindner C
Liu Y
Karaghiosoff K
Maryasin B
Zipse H
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2013 May 10; Vol. 19 (20), pp. 6429-34. Date of Electronic Publication: 2013 Mar 22.
Publication Year :
2013

Abstract

The aza-Morita-Baylis-Hillman (aza-MBH) reaction has been studied in a variety of solvents, a selection of imine substrates and with various combinations of PPh3 and para-nitrophenol as the catalyst system. The measured kinetic data indicates that the effects of solvent and protic co-catalyst are strongly interdependent. These results are most easily reconciled with a mechanistic model involving the reversible protonation of zwitterionic intermediates in the catalytic cycle, which is also supported by (31)P NMR spectroscopy and quantum chemical studies.<br /> (Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3765
Volume :
19
Issue :
20
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
23526632
Full Text :
https://doi.org/10.1002/chem.201204006