Friedel-crafts alkylation of benzene with (polychloromethyl)silanes
- Friedel-crafts alkylation of benzene with (polychloromethyl)silanes
- 유복렬; 김정현; 조봉관; 정일남
- alkylation; (Polychloromethyl)silanes; (Dichloromethyl)silanes; (Trichloromethyl)silanes; (Diphenylmethyl)silanes; (Triphenylmethyl)silanes; Aluminum chloride
- Issue Date
- Journal of organometallic chemistry
- VOL 631, NO 1, 36-40
- (Polychloromethyl)silanes (Cl3−mMemSiCH3−nCln: m=0–3; n=2, 3) reacted with excess benzene in the presence of aluminum
chloride to give (polyphenylmethyl)silanes. Such reactions occurred at the temperatures ranging from room temperature (m=2,
3; n=2) to 80°C (m=0, 1; n=2, 3), indicating that the reactivity increases with increasing the number (m) of electron-donating
methyl-group(s) at the silicon. In particular, (dichloromethyl)silanes with two or three methyl groups at the silicon (m=2 or 3;
n=2) underwent the alkylation and the decomposition of their products at room temperature. The reaction with
(dichloromethyl)trimethylsilane occurred immediately at room temperature to give no (diphenylmethyl)trimethylsilane, but
diphenylmethane and trimethylchlorosilane via the decomposition of alkylation product. (Trichloromethyl)silanes (m=0, 1; n=3)
reacted with excess benzene to give (triphenylmethyl)silanes as major products and the unusual (diphenylmethyl)silanes as minor.
It was found that unusual (diphenylmethyl)silanes were formed by the decomposition of (triphenylmethyl)silanes under the
reaction condition. In the alkylation to benzene, the reactivity of (polychloromethyl)silanes (Cl3−mMemSiCH3−nCln: m=0–3;
n=2, 3) decreases in the following order: m=3 2 1 0; n=3 2. © 2001 Elsevier Science B.V. All rights reserved.
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