ChemInform Abstract: ALKYLATION OF FERROCENE. I. REACTION OF FERROCENE WITH ETHYLENECHLOROHYDRIN AND DIBROMOETHANE

Твердохлебов, В. П.; Polyakov, B. V.; Целинский, И. В.; Golubeva, L. I.

doi:10.1002/chin.198313304

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“…These researchers also reacted ferrocene with ethylene and obtained a 20.5% yield of alkylated product . Alkylations of ferrocene with other alkylating agents such as 2-chloroethanol, 1,2-dibromoethane, methyl chloromethyl ether, and chloro- and aminoorganosilanes have been reported, but the yields were poor except for the alkylation involving 1,2-dibromoethane. Alkylation with 1,2-dibromoethane gave a mixture of mono- and polyethylated products in approximately 90% yield; however, 30 equiv of 1,2-dibromoethane and 5 equiv of AlCl 3 were required.…”

Section: Introductionmentioning

confidence: 99%

Lewis Acid-Catalyzed Friedel−Crafts Alkylation of Ferrocene with Allylchlorosilanes

et al. 2000

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Friedel-Crafts alkylations of ferrocene, 1, with allylchlorosilanes in the presence of Lewis acid catalysts under mild conditions gave regiospecific [1-methyl-2-(alkylchlorosilyl)ethyl]ferrocenes in fair to good yields depending upon the substituents on silicon, along with small amounts of dialkylated products. The alkylation of ferrocene with 1.2 equiv of (2-methylallyl)dimethylchlorosilane, 2b, at 0 °C gave monoalkylated ferrocene 3b and an isomeric mixture of dialkylated products in 76% and 4% yields, respectively. The yield of the dialkylated ferrocene mixture increased to 21% when 2 equiv of alkylating agent 2b was used. The two components of the dialkylated product mixture were identified as 1,1′-dialkylated ferrocene 4b (17%), and 1,3-dialkylated ferrocene 4b′ (4%). A higher yield of the 1,1′-diadduct compared to the 1,3-diadduct indicates that the electron-donating alkylsilyl group does not greatly enhance a second alkylation on the same ring. The reactivities of allylchlorosilanes in the ferrocene alkylations decrease in the following order: allyldialkylchlorosilane > allyl(alkyl)dichlorosilane . allyldichlorosilane ≈ allyltrichlorosilane. The catalytic efficiencies of Lewis acids for the alkylations decrease in the following order: HfCl 4 > ZrCl 4 > AlCl 3 > AlBr 3 >TiCl 4 .

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Section: Introductionmentioning

confidence: 99%

Lewis Acid-Catalyzed Friedel−Crafts Alkylation of Ferrocene with Allylchlorosilanes

et al. 2000

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ChemInform Abstract: ALKYLATION OF FERROCENE. I. REACTION OF FERROCENE WITH ETHYLENECHLOROHYDRIN AND DIBROMOETHANE

Abstract: Ferrocen (I) bildet mit Dibromethan (II) in Gegenwart von AlCl3/NaBH4 ein Gemisch der literaturbekannten Alkylferrocene (IV)‐(VII).

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Lewis Acid-Catalyzed Friedel−Crafts Alkylation of Ferrocene with Allylchlorosilanes

Lewis Acid-Catalyzed Friedel−Crafts Alkylation of Ferrocene with Allylchlorosilanes

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