Formation of Disilanes in the Reaction of Stable Silylenes with Halocarbons

• Published in: Journal of the American Chemical Society Vol. 127; no. 42; pp. 14730 - 14738
• Main Authors: Moser, Daniel F, Naka, Akinobu, Guzei, Ilia A, Müller, Thomas, West, Robert
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 26-10-2005
• Subjects: Chemistry; Crystallography, X-Ray; Exact sciences and technology; Free radicals chemistry; Hydrocarbons, Halogenated - chemistry; Models, Molecular; Molecular Structure; Organic chemistry; Oxidation-Reduction; Reactivity and mechanisms; Silanes - chemical synthesis; Silanes - chemistry; Silicon Compounds - chemistry; Five membered ring; Halogenated hydrocarbon; Organic silylene; Organic free biradical; Reaction mechanism; Organic silane; NMR spectrometry; Nitrogen silicon heterocycle; Experimental study; Molecule radical reaction; Chemical coupling
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja052584g

Reactions of stable silylenes 1 and 2 with a variety of halogenated organic compounds have been studied. Depending on the nature of the halocarbon, the products can be disilanes, LSiX−LSiR, or monosilanes, LSiXR, or a mixture of both types of products. Hexachloroethane reacts with the silylenes to give mainly the dichlorodisilane, LSiX−LSiX. The experimental results are rationalized in terms of several related free-radical chain mechanisms.