The biochemistry of carbon–halogen compounds

Doonan, Shawn

doi:10.1002/9780470771280.ch13

Cited by 2 publications

(1 citation statement)

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“…The growing demand for organobromines we use in our society as intermediates, − materials, , flame retardants, emulsifiers, agrochemicals, or pharmaceuticals, , is covered by hydrocarbon functionalization that mechanistically proceed via nucleophilic substitution, free radical chain reaction, or electrophilic-bromination. The largest proportion of technically produced organobromines thereby originates from reactions between molecular bromine − and carbon nucleophiles. , …”

Section: Introductionmentioning

confidence: 99%

Vanadium(V)-Catalyzed Oxidative Bromination of Acid Labile Alkenols and Alkenes in Alkyl Carbonates

Brücher

Hartung

2011

ACS Catal.

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Molecular bromine is formed from bromide and tert-butyl hydroperoxide under mild and neutral conditions. The oxidation is catalyzed by vanadium(V)-complexes and requires bromide- and proton- aliquots that are slowly released from a 3-bromopropionic acid-bromide buffer in solutions of alkyl carbonates. In such an environment, bromocyclization of acid labile alkenols occurs without hydrolytically cleaving acetal- or ester-protecting groups. 4-Pentenols having methyl- and/or phenyl-groups attached to the terminal carbon atom of the alkenol double bond undergo 6-endo-selective ring closures if subjected to oxidative bromination and provide bromotetrahydropyrans in synthetically useful yields. Application of the new procedure affords a hexasubstituted tetrahydropyran-building block en route to synthesis of the marine natural product aplysiapyranoid A.

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Section: Introductionmentioning

confidence: 99%

Vanadium(V)-Catalyzed Oxidative Bromination of Acid Labile Alkenols and Alkenes in Alkyl Carbonates

Brücher

Hartung

2011

ACS Catal.

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Biochemistry of halogenated organic compounds

Kirk¹

2009

Patai's Chemistry of Functional Groups

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Introduction Biohalogenation Biochemistry of the Thyroid Hormones Biochemistry of Selected Halogenated Organic Compounds Biochemistry of Polyhalogenated Organic Molecules Metabolism of Halogenated Organic Compounds—Biodehalogenation

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The biochemistry of carbon–halogen compounds

Cited by 2 publications

References 125 publications

Vanadium(V)-Catalyzed Oxidative Bromination of Acid Labile Alkenols and Alkenes in Alkyl Carbonates

Vanadium(V)-Catalyzed Oxidative Bromination of Acid Labile Alkenols and Alkenes in Alkyl Carbonates

Biochemistry of halogenated organic compounds

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