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

DC Braddock, J Clarke, HS Rzepa

Index: Christopher Braddock; Clarke, James; Rzepa, Henry S. Chemical Communications, 2013 , vol. 49, # 95 p. 11176 - 11178

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Citation Number: 6

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.