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

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

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

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2451-2460
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	17
DOIs	https://doi.org/10.1039/b407293f
Publication status	Published - 7 Sept 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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10.1039/b407293f

Cite this

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

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.",

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author = "Stephen Hermitage and Howard, {Judith A K} and David Jay and Pritchard, {Robin G.} and Probert, {Michael R.} and Andrew Whiting",

year = "2004",

month = sep,

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doi = "10.1039/b407293f",

language = "English",

volume = "2",

pages = "2451--2460",

journal = "Organic and Biomolecular Chemistry",

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AU - Hermitage, Stephen

AU - Howard, Judith A K

AU - Jay, David

AU - Pritchard, Robin G.

AU - Probert, Michael R.

AU - Whiting, Andrew

PY - 2004/9/7

Y1 - 2004/9/7

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KW - 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 mec

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/cc7yn4y&sid=DataCite

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VL - 2

SP - 2451

EP - 2460

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -

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

Abstract

Keywords

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CCDC 237039: Experimental Crystal Structure Determination

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

Abstract

Keywords

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Other files and links

Fingerprint

Datasets

CCDC 237039: Experimental Crystal Structure Determination

Cite this