Some Organosilicon Compounds Containing Long-Chained n-Alkyl Groups

Abstract

A series of tetra-n-alkyl-, tri-n-alkylaryl-, and n-alkyltriarylsilanes, as well as intermediate compounds, have been prepared for potential use as hydraulic fluids or lubricants. Each compound contains at least one long-chained n-alkyl group having from ten to eighteen carbon atoms. Some aspects of the various means of preparing these compounds are discussed.

Preparation of Covalent Long-Chain Trialkylstannyl and Trialkylsilyl Salts and an Examination of their Adsorption on Gold

“…(See the Supporting Information.) Aryloctadecylsilanes were prepared according to the procedure developed by Gilman et al 1-Bromooctadecane was converted to octadecylmagnesium bromide and treated with neat chlorosilane to obtain silanes 8 − 14 . Most of the chlorosilanes were commercially available, and p -anisyltrichlorosilane was synthesized as reported by Powell and Fu …”

Synthesis and Properties of Intramolecularly Base-Stabilized (Disilanyl−silylene)ruthenium and -iron Complexes

“…Benzene- d 6 , hexane, and toluene for sealed-tube preparation were dried with a potassium mirror and degassed under high vacuum. Cp 2 Ru 2 (CO) 4 , Cp 2 Fe 2 (CO) 4 , ClMe 2 SiSiMe 2 SiMe 2 Cl, PhMe 2 SiCl, i Pr 2 SiCl 2 , and ClMe 2 Si(SiMe 2 ) 2 SiMe 2 Cl were prepared according to published procedures. Other chemicals were used as received from commercial sources.…”

Up-Scale Synthesis of p-(CH2═CH)C6H4CH2CH2CH2Cl and p-ClC6H4SiR3 by CuCN-Catalyzed Coupling Reactions of Grignard Reagents with Organic Halides

“…Its preparation was attempted by the reaction of 3 equiv of n -BuMgBr with SiCl 4 , but the desired product was isolated in a low yield (12%) with a main n -Bu 2 SiCl 2 (35%) (Scheme b) . Similarly, preparation of ( n -hexadecyl) 3 SiCl was attempted by reacting 2 equiv of ( n -hexadecyl)­MgBr with ( n -hexadecyl)­SiCl 3 , but the desired compound was not cleanly isolated . Thus, detoured routes were developed for the synthesis of R 3 SiCl type compounds.…”

“…Thus, detoured routes were developed for the synthesis of R 3 SiCl type compounds. The most frequently employed method is the route via R 3 SiH, as described for the synthesis of ( n -octyl) 3 SiCl in Scheme a . Another route involves reacting RMgBr with Si­(OEt) 4 to obtain R 3 SiOEt, which was subsequently treated with NH 4 Cl in concentrated H 2 SO 4 to generate the desired n-Bu 3 SiCl or Et 3 SiCl (Scheme c). , …”