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

Stephen Hermitage, Judith A K Howard, David Jay, Robin G. Pritchard, Michael R. Probert, Andrew Whiting

    Research output: Contribution to journalArticlepeer-review

    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.
    Original languageEnglish
    Pages (from-to)2451-2460
    Number of pages9
    JournalOrganic and Biomolecular Chemistry
    Volume2
    Issue number17
    DOIs
    Publication statusPublished - 7 Sep 2004

    Keywords

    • Catalysis (acid, Lewis; crystal structure and NMR on non-concertedness aza-Diels-Alder reaction mechanism of N-aryl imines under Lewis-acid catalysis); Diels-Alder reaction (aza-; crystal structure and NMR on non-concertedness aza-Diels-Alder reaction mechanism of N-aryl imines under Lewis-acid catalysis); Reaction mechanism (crystal structure and NMR on non-concertedness aza-Diels-Alder reaction mechanism of N-aryl imines under Lewis-acid catalysis); Alkadienes; Cycloalkadienes Role: CPS (Chemical process), PEP (Physical, engineering or chemical process), RCT (Reactant), PROC (Process), RACT (Reactant or reagent) (crystal structure and NMR on non-concertedness aza-Diels-Alder reaction mechanism of N-aryl imines under Lewis-acid catalysis)

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