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Issue 95, 2013
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Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide – Favorskii manifold

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Abstract

DMDO epoxidation of bromoallenes gives directly α,β-unsaturated carboxylic acids under the reaction conditions. Calculated (ωB97XD/6-311G(d,p)/SCRF = acetone) potential energy surfaces and 2H- and 13C-labeling experiments are consistent with bromoallene oxide intermediates which spontaneously rearrange via a bromocyclopropanone in an intersecting bromoallene oxide – Favorskii manifold.

Graphical abstract: Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide – Favorskii manifold

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Article information


Submitted
03 Sep 2013
Accepted
07 Oct 2013
First published
23 Oct 2013

This article is Open Access

Chem. Commun., 2013,49, 11176-11178
Article type
Communication

Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide – Favorskii manifold

D. Christopher Braddock, J. Clarke and H. S. Rzepa, Chem. Commun., 2013, 49, 11176
DOI: 10.1039/C3CC46720A

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