V. Mironov, V. V. Nepomnina, L. Leites
Mar 1, 1960
Citations
0
Influential Citations
0
Citations
Journal
Russian Chemical Bulletin
Abstract
1. In the dehydrochlorination of trichloro(1,2-dichloroisopropyl)silane with aluminum chloride, trichloro-(2-chloropropenyl)silane is formed. This isomerization is a special case of a general rearrangement undergone by all trichloro(1,2-dichloroalkyl)silanes when dehydrochlorinated with aluminum chloride. 2. A mechanism is proposed for this new arrangement in the organic chemistry of silicon; it consists in partial or complete migration of a trichlorosilyl group from the 1- to the 2-carbon atom after the elimination of the 2-chlorine atom, which leads to the formation of trichloro(2-chloro-l-alkenyl)silanes. 3. Whereas the dehydrochlorination of a trichloro(1,2-dichloroalkyl)silane gives only one unsaturated compound, the same reaction with a trichloro(2,3-dichloroalkyl)silane gives a mixture of two different unsaturated organosilicon compounds. 4. A method was developed for the synthesis of dichloro(3-chloroalkyl)methylsilanes under mild conditions without use of an autoclave, and it was shown that unsaturated compounds can be synthesized in good yield by the pyrolysis of these compounds. 5. In dehydrohalogenation, a bromine atom in an alkyl chain of an organosilicon compound is much more readily eliminated than an analogous chlorine atom.