Direct Conversion of Bromohydrins to Ketones by a Free Radical Elimination of Hydrogen Bromide1

Secondary β-bromo alcohols can be transformed directly to ketones in very good yields by a free radical process. Tertiary β-bromo alcohols do not react while the primary ones are transformed to aldehydes in lower yields. The reaction involves an abstraction of a hydrogen atom α to an OH group, follo...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-01, Vol.67 (1), p.312-313
Main Authors: Dolenc, Darko, Harej, Maja
Format: Article
Language:English
Online Access:Get full text
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Summary:Secondary β-bromo alcohols can be transformed directly to ketones in very good yields by a free radical process. Tertiary β-bromo alcohols do not react while the primary ones are transformed to aldehydes in lower yields. The reaction involves an abstraction of a hydrogen atom α to an OH group, followed by elimination of the bromine atom and subsequent tautomerization of an enol to a ketone.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016113y