other reagents used in one important respect. They are incapable of providing a nucleophilic anion for combination with silicon. Also, a driving force for dehydrohalogenation with quinoline, i.e., formation of the hydrochloride salt, is absent for ^-elimination involving silicon. Silicon halides do not form analogous salts with quinoline. Summary 1. Further studies of ^-eliminations involving silicon have been carried out with /3-chloroethyl-diethylchlorosilane, /3-chloroethyldiethylfluorosilane and /3-chloroethyltriethylsilane.2. These probably give /3-eliminations by mechanisms similar to those established for the dehydrohalogenation of ordinary organic halides with electrophilic and nucleophilic reagents.3. Heating ¡3-chloroethyltriethylsilane gives /3-elimination in the absence of any added reagent.4. The /3-eliminations reported are attributed to the electropositive nature of silicon compared to carbon and hydrogen. State College, Pa.
Vol. 70 ion. The Si-C bond is broken and a new bond between silicon and hydroxyl is formed. The inertness of this ester to water is likely due to a concentration of either hydroxyl or hydrogen ions insufficient to permit the operation of mechanisms (2) or (3). Reaction with ethanol may be attributed in part to the homogeneity of the system.The action of anhydrous hydrogen chloride upon ethyl trimethylsilylacetate may be pictured by mechanism (4).
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