Fluorous Solvents for Slow Chlorination and Bromination of Alcohols

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 19 (2014) pp 247-251

Fluorous Solvents for Slow Chlorination and Bromination of Alcohols

Elisabeth Rukmini Goei^†, Susan Sonchik Marine*^,‡, Richard T. Taylor^†, Angela French^‡, Amanda E. Stewart^‡

^†Department of Chemistry and Biochemistry, Miami University, 651 East High St.; Oxford, OH 45056; ^‡Department of Chemistry and Biochemistry, Miami University Middletown, 4200 North University Blvd.; Middletown, OH 45042, mariness@MiamiOH.edu
Received April 24, 2014. Accepted June 28, 2014.

Published: 14 August 2014

Abstract. By constructing a fluorous liquid membrane between two organic phases, one can mediate the mixing of reagents between the phases. Curran [1] showed that alcohols could be converted to chlorides by the action of thionyl chloride through the fluorous phase. Most of Curran’s examples were alcohols incapable of rearrangement or elimination. In a discovery-based experiment, a sophomore organic chemistry class and a chemical technology class examined this reaction using a diverse set of alcohols. The products were analyzed by GC/MS, and the product ratios could be related to the competition between substitution, elimination, and rearrangement. Similar conversions of alcohols to bromides using SOBr₂ and PBr₃ were also undertaken. The experiment provided an introduction to fluorous chemistry and allowed students to explore the relationship between reaction mechanisms.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: mariness@MiamiOH.edu )

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Supporting Materials:

Two supporting files are available. Student Handout for an Undergraduate Organic Laboratory: “Fluorous Chemistry Lab” and Student Handout for a Chemical Technology Laboratory: “Triphasic Chlorination of Alcohols”e (176 KB).