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.