Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2015-10-08 , DOI: 10.1016/j.jfluchem.2015.10.002 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
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.
中文翻译:
一种方便实用的选择性制备氘代氟代烃的方法
报道了对从1-碘代氟代氟代烷选择性合成1-氘代氟代氟代烷的有效和实用条件的发展进行的详细研究。最佳条件包括在密封的Schlenk管中在金属锌存在下,在约170°C的D 2 O中处理碘代前体,以产生59%的1-氘1,1,2,2,3产率。 ,3,4,4,4-九氟丁烷。相同的方法被成功地应用于两个高级同系物,以产生1 -氘代1,1,2,2,3,3,4,4,5,5,5-十一氟戊烷和1-氘代1,1,2, 2,3,3,4,4,5,5,6,6,6,6-三氟氟己烷的产率分别为64%和56%。令人惊讶的是,使用这种方法,甚至可以以69%的产率合成非全氟化产物6-氘-1,1,1,2,2,3,3,4,4-九氟己烷。