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Taming Bromine Azide for Use in Organic Solvents─Radical Bromoazidations and Alcohol Oxidations.

ABSTRACT: The formation of bromine azide from the bisazidobromate(I) anion or alternatively from Zhdankin's reagent, using a phosphonium bromide salt as a common starting point, is reported. After homolytic cleavage in the presence of alkenes or alcohols either 1,2-functionalization or alternatively the selective oxidation of secondary alcohols in the presence of primary alcohols occur. The scopes and limitations of the use of BrN₃ are covered.

SUBMITTER: Schulz G

PROVIDER: S-EPMC10028602 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Taming Bromine Azide for Use in Organic Solvents─Radical Bromoazidations and Alcohol Oxidations.

Schulz Göran G George Vincent V Taser Daghan D Kirschning Andreas A

The Journal of organic chemistry 20230223 6

The formation of bromine azide from the bisazidobromate(I) anion or alternatively from Zhdankin's reagent, using a phosphonium bromide salt as a common starting point, is reported. After homolytic cleavage in the presence of alkenes or alcohols either 1,2-functionalization or alternatively the selective oxidation of secondary alcohols in the presence of primary alcohols occur. The scopes and limitations of the use of BrN<sub>3</sub> are covered. ...[more]

PMID: 36821827

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