Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 12, Pages 2278-2285Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001676
Keywords
Allenes; Bromine; Electrophilic addition; Regioselectivity; Bromohydroxylation
Categories
Funding
- National Natural Science Foundation of China [20732005, 20972135]
- Zhejiang Provincial Science Foundation of China [Y4090217]
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A regioselective bromohydroxylation reaction of simple allenes affording 2-bromoalken-3-ols in moderate-to-good yields has been developed by using NBS as the electrophilic reagent in a mixture of 1,4-dioxane/H2O (1:1) at room temperature. Through this study it has been concluded that the regioselectivity is determined by various factors including steric and electronic effects of the substituents of the allene moiety.
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