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

See Wing Lo; Edwin Law; Matthew Y. Lui; Xi Guang Wei; Kai Chung Lau; Chui Y. Ma; Margaret B. Murphy; István T. Horváth

doi:10.1039/c4qo00192c

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

See Wing Lo, Edwin Law, Matthew Y. Lui, Xi Guang Wei, Kai Chung Lau^*, Chui Y. Ma, Margaret B. Murphy^*, István T. Horváth^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1180-1187
Number of pages	8
Journal	Organic Chemistry Frontiers
Volume	1
Issue number	10
DOIs	https://doi.org/10.1039/c4qo00192c
Publication status	Published - 1 Dec 2014
Externally published	Yes

Scopus Subject Areas

Organic Chemistry

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title = "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.",

author = "Lo, {See Wing} and Edwin Law and Lui, {Matthew Y.} and Wei, {Xi Guang} and Lau, {Kai Chung} and Ma, {Chui Y.} and Murphy, {Margaret B.} and Horv{\'a}th, {Istv{\'a}n T.}",

note = "Funding Information: We are grateful for the continuous support and help of the Technical Officers of the Department of Biology and Chemistry of City University of Hong Kong. This work was funded by the City University of Hong Kong, project number 7002604 (2010). Publisher Copyright: {\textcopyright} the Partner Organisations 2014",

year = "2014",

month = dec,

day = "1",

doi = "10.1039/c4qo00192c",

language = "English",

volume = "1",

pages = "1180--1187",

journal = "Organic Chemistry Frontiers",

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publisher = "Royal Society of Chemistry",

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T1 - Development of sustainable fluorous chemistry

T2 - the synthesis and characterization of fluorous ethers with nonafluoro-tert-butoxy groups

AU - Lo, See Wing

AU - Law, Edwin

AU - Lui, Matthew Y.

AU - Wei, Xi Guang

AU - Lau, Kai Chung

AU - Ma, Chui Y.

AU - Murphy, Margaret B.

AU - Horváth, István T.

N1 - Funding Information: We are grateful for the continuous support and help of the Technical Officers of the Department of Biology and Chemistry of City University of Hong Kong. This work was funded by the City University of Hong Kong, project number 7002604 (2010). Publisher Copyright: © the Partner Organisations 2014

PY - 2014/12/1

Y1 - 2014/12/1

N2 - 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.

AB - 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.

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U2 - 10.1039/c4qo00192c

DO - 10.1039/c4qo00192c

M3 - Article

AN - SCOPUS:84925280414

VL - 1

SP - 1180

EP - 1187

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 10

ER -

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

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