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An Efficient Approach to 2‐Bromoalken‐3‐ols by Regioselective Bromohydroxylation Reaction of Simple Allenes with NBS
Author(s) -
Kong Wangqing,
Guo Binjie,
Fu Chunling,
Ma Shengming
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001676
Subject(s) - regioselectivity , chemistry , allene , steric effects , reagent , moiety , electrophile , organic chemistry , computational chemistry , medicinal chemistry , catalysis
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/H 2 O (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.