A convenient and practical method for the selective preparation of deuterofluorocarbons

David P. Richardson; Gordon S. Bauer; Andrew A. Bravo; Michael Drzyzga; Tina Motazedi; Emma M. Pelegri-O'Day; Shirish Poudyal; Daniel L.M. Suess; John W. Thoman

doi:10.1016/j.jfluchem.2015.10.002

A convenient and practical method for the selective preparation of deuterofluorocarbons

David P. Richardson, Gordon S. Bauer, Andrew A. Bravo, Michael Drzyzga, Tina Motazedi, Emma M. Pelegri-O'Day, Shirish Poudyal, Daniel L.M. Suess, John W. Thoman

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

4 Scopus citations

Abstract

A detailed study of the development of efficient and practical conditions for the selective synthesis of 1-deuterononafluorobutane from 1-iodononafluorobutane is reported. The optimal conditions involve treatment of the iodo-precursor in D₂O at ∼170 °C in the presence of metallic zinc in a sealed Schlenk tube to give a 59% yield of 1-deutero-1,1,2,2,3,3,4,4,4-nonafluorobutane. The same method was applied successfully to two higher homologues to produce 1-deutero-1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane and 1-deutero-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane in yields of 64% and 56%, respectively. Surprisingly, even the non-perfluorinated product 6-deutero-1,1,1,2,2,3,3,4,4-nonafluorohexane could be synthesized in 69% yield with this method.

Original language	English (US)
Pages (from-to)	208-215
Number of pages	8
Journal	Journal of Fluorine Chemistry
Volume	180
DOIs	https://doi.org/10.1016/j.jfluchem.2015.10.002
State	Published - Dec 1 2015

Keywords

F NMR spectroscopy
Deuteration
Deuteroperfluroroalkanes
Iodoperfluoroalkanes
Perfluoroalkanes
Zinc
Zinc chloride

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.jfluchem.2015.10.002

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@article{2e943ed89ea94dd5b3972b113f0fd9f3,

title = "A convenient and practical method for the selective preparation of deuterofluorocarbons",

abstract = "A detailed study of the development of efficient and practical conditions for the selective synthesis of 1-deuterononafluorobutane from 1-iodononafluorobutane is reported. The optimal conditions involve treatment of the iodo-precursor in D2O at ∼170 °C in the presence of metallic zinc in a sealed Schlenk tube to give a 59\% yield of 1-deutero-1,1,2,2,3,3,4,4,4-nonafluorobutane. The same method was applied successfully to two higher homologues to produce 1-deutero-1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane and 1-deutero-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane in yields of 64\% and 56\%, respectively. Surprisingly, even the non-perfluorinated product 6-deutero-1,1,1,2,2,3,3,4,4-nonafluorohexane could be synthesized in 69\% yield with this method.",

keywords = "F NMR spectroscopy, Deuteration, Deuteroperfluroroalkanes, Iodoperfluoroalkanes, Perfluoroalkanes, Zinc, Zinc chloride",

author = "Richardson, \{David P.\} and Bauer, \{Gordon S.\} and Bravo, \{Andrew A.\} and Michael Drzyzga and Tina Motazedi and Pelegri-O'Day, \{Emma M.\} and Shirish Poudyal and Suess, \{Daniel L.M.\} and Thoman, \{John W.\}",

note = "Funding Information: This work was supported by the President and Trustees of Williams College. We thank Deborah Morandi for assistance with preparation and submission of the manuscript. Publisher Copyright: {\textcopyright} 2015 The Authors. Published by Elsevier B.V.",

year = "2015",

month = dec,

day = "1",

doi = "10.1016/j.jfluchem.2015.10.002",

language = "English (US)",

volume = "180",

pages = "208--215",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - A convenient and practical method for the selective preparation of deuterofluorocarbons

AU - Richardson, David P.

AU - Bauer, Gordon S.

AU - Bravo, Andrew A.

AU - Drzyzga, Michael

AU - Motazedi, Tina

AU - Pelegri-O'Day, Emma M.

AU - Poudyal, Shirish

AU - Suess, Daniel L.M.

AU - Thoman, John W.

N1 - Funding Information: This work was supported by the President and Trustees of Williams College. We thank Deborah Morandi for assistance with preparation and submission of the manuscript. Publisher Copyright: © 2015 The Authors. Published by Elsevier B.V.

PY - 2015/12/1

Y1 - 2015/12/1

N2 - A detailed study of the development of efficient and practical conditions for the selective synthesis of 1-deuterononafluorobutane from 1-iodononafluorobutane is reported. The optimal conditions involve treatment of the iodo-precursor in D2O at ∼170 °C in the presence of metallic zinc in a sealed Schlenk tube to give a 59% yield of 1-deutero-1,1,2,2,3,3,4,4,4-nonafluorobutane. The same method was applied successfully to two higher homologues to produce 1-deutero-1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane and 1-deutero-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane in yields of 64% and 56%, respectively. Surprisingly, even the non-perfluorinated product 6-deutero-1,1,1,2,2,3,3,4,4-nonafluorohexane could be synthesized in 69% yield with this method.

AB - A detailed study of the development of efficient and practical conditions for the selective synthesis of 1-deuterononafluorobutane from 1-iodononafluorobutane is reported. The optimal conditions involve treatment of the iodo-precursor in D2O at ∼170 °C in the presence of metallic zinc in a sealed Schlenk tube to give a 59% yield of 1-deutero-1,1,2,2,3,3,4,4,4-nonafluorobutane. The same method was applied successfully to two higher homologues to produce 1-deutero-1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane and 1-deutero-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane in yields of 64% and 56%, respectively. Surprisingly, even the non-perfluorinated product 6-deutero-1,1,1,2,2,3,3,4,4-nonafluorohexane could be synthesized in 69% yield with this method.

KW - F NMR spectroscopy

KW - Deuteration

KW - Deuteroperfluroroalkanes

KW - Iodoperfluoroalkanes

KW - Perfluoroalkanes

KW - Zinc

KW - Zinc chloride

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DO - 10.1016/j.jfluchem.2015.10.002

M3 - Article

AN - SCOPUS:84944715757

SN - 0022-1139

VL - 180

SP - 208

EP - 215

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

A convenient and practical method for the selective preparation of deuterofluorocarbons

Abstract

Keywords

ASJC Scopus subject areas

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