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Domino Diels-Alder reactions of N-methoxyethyl-7-oxa-norbornadiene-2,3- dicarboximide : an elusive, highly reactive dienophile

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journal contribution
posted on 2017-12-06, 00:00 authored by D Margetic, Douglas Butler, Ronald Warrener, Y Murata
Flash vacuum pyrolysis (FVP) has been used to generate the novel 7-oxa-norbornadiene-2,3-dicarboxylic imide that in situ gave an unprecedented cycloaddition reaction cascade with the imidofuran, a side-product of FVP. Stereoselectivity of cycloadditions was studied with the aid of density functional calculations, which fully support observed exo/endo-selectivity.

Funding

Category 1 - Australian Competitive Grants (this includes ARC, NHMRC)

History

Volume

67

Issue

8

Start Page

1580

End Page

1588

Number of Pages

9

eISSN

1464-5416

ISSN

0040-4020

Location

United Kingdom

Publisher

Pergamon

Publisher DOI

Full Text URL

Language

en-aus

Peer Reviewed

  • Yes

Open Access

  • No

External Author Affiliations

Centre for Molecular Architecture; Institut Ruđer Bos̆ković; Kyōto Daigaku; TBA Research Institute;

Era Eligible

  • Yes

Journal

Tetrahedron.

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    Categories

    Keywords

    DFT calculationsDiels-Alder reactionFlash vacuum pyrolysisFuranTransition statesOrganic Chemistry not elsewhere classified

    Licence

    CQUniversity General 1.0

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