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
UR - http://www.scopus.com/inward/record.url?scp=84944715757&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84944715757&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2015.10.002
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 -