D. Lahiouhel, B. Améduri, B. Boutevin
2001
Citations
0
Influential Citations
34
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract The radical addition of 1-iodoperfluorohexane ( 1 ) to allyl alcohol (2-propen-1-ol) ( 2 ) was investigated in the presence of various initiating systems (photochemically or in the presence of redox catalysts or organic initiators), leading to C 6 F 13 CH 2 CHICH 2 OH ( 3 ) in various yields. A scale of efficiency of the involved radical system was proposed, triphenylphosphine and AIBN yielding the best conversions of 1 . Interestingly, AIBN, when added three times in the course of the reaction was the most suitable for an almost quantitative consumption of 1 . Then, 3 was reduced to C 6 F 13 C 3 H 6 OH ( 4 ) in high yields by tributylstannane. Such a two-step procedure was extrapolated to the preparation of the fluorinated telechelic diol from 1,6-diiodoperfluorohexane ( 5 ). First, the formations of both the 1-to-1 monoadduct ( 6 ) and 1-to-2 α,ω-diadduct ( 7 ) were noted and discussed: optimised conditions enabled production of 7 in 81% yield with a complete conversion of 5 . Then, telechelic diol HOC 3 H 6 C 6 F 12 C 3 H 6 OH ( 8 ) was synthesised selectively in 88% yield, from the reduction of the iodine atoms of 7 by tributylstannane. 1 H , 19 F and 13 C NMR spectroscopies allowed characterisation of all the intermediates and products without ambiguity.