title: Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide--Favorskii manifold.
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 (2)H- and (13)C-labeling experiments are consistent with bromoallene oxide intermediates which spontaneously rearrange via a bromocyclopropanone in an intersecting bromoallene oxide - Favorskii manifold.
authors.affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ, UK. c.braddock@imperial.ac.uk.
authors.forename: D Christopher
authors.initials: DC
authors.lastname: Braddock
authors.forename: James
authors.initials: J
authors.lastname: Clarke
authors.forename: Henry S
authors.initials: HS
authors.lastname: Rzepa
mesh_terms: D000475:Alkenes / Q000737:chemistry / Q000378:metabolism*; D001966:Bromine / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D010087:Oxides / Q000737:chemistry*; D000461:Rhodophyta / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000475:Alkenes; D002247:Carbon Isotopes; D002264:Carboxylic Acids; D004852:Epoxy Compounds; D010087:Oxides; D003903:Deuterium; D001966:Bromine