Chloroplatinic Acid-catalyzed Reduction of Haloalkanes
The Hydrosilane Reduction IV
1969 Volume 27 Issue 8 Pages 747-753
Details
1969 Volume 27 Issue 8 Pages 747-753
A hydrogen-halogen exchange reaction between a hydrosilane and a chloroalkane or a bromoalkane was found to occur under rather mild conditions in the presence of chloroplatinic acid as a catalyst. For example, carbon tetrachloride was treated with triethylsilane at 75°C for 10 hr to obtain chloroform and triethylchlorosilane in 68 and 95% yields respectively. Varieties of gem-polyhaloalkanes were similarly reduced with ease to form mainly the first step reduction products. In general, the yield of the halosilane was almost quantitative, whereas that of the reduced haloalkane was rather poor. The feature of this reaction and that of the previously reported homolytic reduction by hydrosilane are much alike.
Thus, the reactivity of halogen atoms decreases in the following order : -CCl2-Cl>-CHCl-Cl>-CH2-Cl2 secondary C-Cl>primary C-Cl, and Br>Cl.
