Issue 10, 2014

Development of sustainable fluorous chemistry: the synthesis and characterization of fluorous ethers with nonafluoro-tert-butoxy groups

Abstract

Nonafluoro-t-butyl propyl (1), allyl (2), and propargyl (3) ethers as well as 1,2-bis(nonafluoro-t-butoxy)ethane (4), 1,3-bis(nonafluoro-t-butoxy)-propane (5), and 1,4-bis(nonafluoro-t-butoxy)-butane (6) were prepared by the reaction of sodium nonafluoro-t-butoxide (7) with the corresponding alkyl halides in good yields. Their fluorous partition coefficients and toxicity were also investigated. Computational studies have shown that 4, 5 and 6 exist in a monomeric form in MeOH–CF3C6F11 and they likely aggregate to form oligomers in PhCH3–CF3C6F11.

Graphical abstract: Development of sustainable fluorous chemistry: the synthesis and characterization of fluorous ethers with nonafluoro-tert-butoxy groups

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jul 2014
Accepted
23 Sep 2014
First published
13 Oct 2014

Org. Chem. Front., 2014,1, 1180-1187

Development of sustainable fluorous chemistry: the synthesis and characterization of fluorous ethers with nonafluoro-tert-butoxy groups

S. Lo, E. Law, M. Y. Lui, X. Wei, K. Lau, C. Y. Ma, M. B. Murphy and I. T. Horváth, Org. Chem. Front., 2014, 1, 1180 DOI: 10.1039/C4QO00192C

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