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Molecules 2016, 21(10), 1325; doi:10.3390/molecules21101325

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

1,2
and
1,2,3,*
1
Department of Physical and Organic Chemistry, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia
2
Jožef Stefan International Postgraduate School, Jamova 39, 1000 Ljubljana, Slovenia
3
Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins CIPKeBiP (Seat at Jožef Stefan Institute), Jamova 39, 1000 Ljubljana, Slovenia
*
Author to whom correspondence should be addressed.
Academic Editors: Joaquín García Álvarez and Jonathan Sperry
Received: 31 August 2016 / Revised: 23 September 2016 / Accepted: 27 September 2016 / Published: 2 October 2016
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
View Full-Text   |   Download PDF [985 KB, uploaded 2 October 2016]   |  

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. View Full-Text
Keywords: halohydrins; halogenation; water; tertiary alcohols; N-halosuccinimides halohydrins; halogenation; water; tertiary alcohols; N-halosuccinimides
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ajvazi, N.; Stavber, S. Transformation of Tertiary Benzyl Alcohols into the Vicinal Halo-Substituted Derivatives Using N-Halosuccinimides. Molecules 2016, 21, 1325.

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