Yoo, BR Kim, JH Lee, HJ Lee, KB Jung, IN 2024-01-21T13:42:04Z 2024-01-21T13:42:04Z 2021-09-05 2000-07-07 0022-328X https://pubs.kist.re.kr/handle/201004/141234 (omega-Chloroalkyl)silanes [Cl3-mMemSi(CH2)(n)-Cl: m = 0-3, n = 1-3] underwent Friedel-Crafts alkylation with benzene in the presence of aluminum chloride to give alkylated products. Such alkylation reactions took place at temperatures ranging from room temperature (m=0-1, n =2, 3; m = 3, n= 1) to 80 (m = 1, 2; n := 1) and 200 degrees C (m =0; n = 1), depending on the substituent(s) of the silicon and the alkylene-chain s:pacer between the silicon and C-CI bond of (omega-chloroalkyl)silanes. In the alkylation to benzene, the reactivities of (omega-chloroalkyl)silanes increase as the number (m) of methyl-group(s) at the silicon and the alkylene length between the silicon and C-CI bond increases. While decomposition of alkylation products was observed at two more methyl groups substituted at silicon in the cases of (chloromethyl)silanes such as (chloromethyl)dimethylchlorosilane and (chloromethyl)trimethylsilane. The reaction with (chloromethyl)trimethylsilane occurred at room temperature to give trimethylchlorosilane, toluene and xylene via a decomposition reaction of the products. No (trimethylsilylmethyI)benzene was formed. In the alkylation to benzene, the reactivity of (omega-chloroalkyl)silanes decreases in the following order: m = 3 > 2 > 1 > 0; n=3>2 much greater than 1. The results are consistent with the stability of the carbocation generated by the complexation of (omega-chloroalkyl)silanes with aluminum chloride. (C) 2000 Elsevier Science S.A. All rights reserved. English ELSEVIER SCIENCE SA 1ST-ROW ELEMENTS ENERGIES IONS Effect of the substituents at the silicon of (omega-chloroalkyl)silanes on the alkylation to benzene Article 10.1016/S0022-328X(00)00319-3 1 JOURNAL OF ORGANOMETALLIC CHEMISTRY, v.605, no.2, pp.239 - 245 JOURNAL OF ORGANOMETALLIC CHEMISTRY 605 2 239 245 scie scopus 000089058300013 2-s2.0-0001496816 Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry Article 1ST-ROW ELEMENTS ENERGIES IONS alkylation Friedel-Crafts alkylation alkylation to benzene (omega-chloroalkyl)silanes Lewis acid aluminum chloride