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Molecules. 2016 Oct 2;21(10). pii: E1325.

Transformation of Tertiary Benzyl Alcohols into the Vicinal Halo-Substituted Derivatives Using N-Halosuccinimides.

Author information

1
Department of Physical and Organic Chemistry, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia. njomzaajvazi@hotmail.com.
2
Jožef Stefan International Postgraduate School, Jamova 39, 1000 Ljubljana, Slovenia. njomzaajvazi@hotmail.com.
3
Department of Physical and Organic Chemistry, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia. stojan.stavber@ijs.si.
4
Jožef Stefan International Postgraduate School, Jamova 39, 1000 Ljubljana, Slovenia. stojan.stavber@ijs.si.
5
Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins CIPKeBiP (Seat at Jožef Stefan Institute), Jamova 39, 1000 Ljubljana, Slovenia. stojan.stavber@ijs.si.

Abstract

The efficiency of direct conversion of tertiary alcohols bearing a β-hydrogen atom to vicinal halohydrins-chlorohydrins and bromohydrins-under green reaction conditions was tested preliminarily on model tertiary benzyl alcohols. Tertiary alcohols were successfully directly halogenated to vicinal halohydrins with N-halosuccinimide in aqueous media. The efficiency of the reaction in water was significantly improved in the presence of sodium dodecyl sulphate as the surfactant.

KEYWORDS:

N-halosuccinimides; halogenation; halohydrins; tertiary alcohols; water

PMID:
27706096
PMCID:
PMC6273677
DOI:
10.3390/molecules21101325
[Indexed for MEDLINE]
Free PMC Article

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