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. © 2013 The Royal Society of Chemistry.

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Braddock, D. C., Clarke, J., & Rzepa, H. S. (2013). Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide - Favorskii manifold. Chemical Communications, 49(95), 11176–11178. https://doi.org/10.1039/c3cc46720a

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