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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.
- 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