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.

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
• Public URL: https://durham-repository.worktribe.com/output/1602143