Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions

Hermitage, S.; Howard, J.A.K.; Jay, D.; Pritchard, R.G.; Probert, M.R.; Whiting, A.

doi:10.1039/b407293f

Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions

Hermitage, S.; Howard, J.A.K.; Jay, D.; Pritchard, R.G.; Probert, M.R.; Whiting, A.

Authors

S. Hermitage

J.A.K. Howard

D. Jay

R.G. Pritchard

M.R. Probert

Professor Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor

Abstract

The reaction of a para-methoxyaniline, ethyl glyoxalate-derived imine with a series of dienes has resulted in products, which initially suggest the operation of different modes of aza-Diels-Alder reaction. However, a more likely explanation is that a common reaction mechanism is operating, involving a step-wise Lewis-acid catalysed process, which only appears to behave similarly to alternative concerted cycloaddition reactions.

Citation

Hermitage, S., Howard, J., Jay, D., Pritchard, R., Probert, M., & Whiting, A. (2004). Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions. Organic and Biomolecular Chemistry, 2(17), 2451-2460. https://doi.org/10.1039/b407293f

Journal Article Type	Article
Publication Date	Aug 1, 2004
Deposit Date	May 3, 2007
Journal	Organic and Biomolecular Chemistry
Print ISSN	1477-0520
Electronic ISSN	1477-0539
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	2
Issue	17
Pages	2451-2460
DOI	https://doi.org/10.1039/b407293f