Issue 15, 2007
From the journal:

Organic & Biomolecular Chemistry

Structures of oxygenated cyclohexa-1,3-diene–maleic anyhydride cycloadducts. Structural evidence suggests a stepwise retro-Diels–Alder reaction

Yit Wooi Goha  and  Jonathan M. White*a  

* Corresponding authors

a School of Chemistry and Bio-21 Institute, The University of Melbourne, Parkville, Vic 3010
E-mail: whitejm@unimelb.edu.au
Fax: +613 93475180
Tel: +613 83442445

Abstract

The structures of a series of cyclohexadiene–maleic anhydride cycloadducts show structural parameters consistent with the early stages of the retro-Diels–Alder (rDA) reaction in the ground state structure. The symmetrical adduct 10 shows effects consistent with a synchronous rDA reaction. An asynchronous rDA reaction is suggested in the structure of 8, and the first evidence suggesting a two-step retro-Diels–Alder mechanism is provided by the deoxygenated adduct 9.

Graphical abstract: Structures of oxygenated cyclohexa-1,3-diene–maleic anyhydride cycloadducts. Structural evidence suggests a stepwise retro-Diels–Alder reaction

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Article information

DOI
https://doi.org/10.1039/B707643F
Article type
Communication
Submitted
21 May 2007
Accepted
14 Jun 2007
First published
20 Jun 2007

Org. Biomol. Chem., 2007,5, 2354-2356

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Structures of oxygenated cyclohexa-1,3-diene–maleic anyhydride cycloadducts. Structural evidence suggests a stepwise retro-Diels–Alder reaction

Y. W. Goh and J. M. White, Org. Biomol. Chem., 2007, 5, 2354 DOI: 10.1039/B707643F

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