Tertiary aluminum butylate

The speed of the reaction depends both on the metal and on the alcohol, increasing as electropositivity iacreases and decreasiag with length and branching of the chain. Thus sodium reacts strongly with ethanol, but slowly with tertiary butyl alcohol. The reaction with alkaU metals is sometimes carried out ia ether, ben2ene, or xylene. Some processes use the metal amalgam or hydride iastead of the free metal. Alkaline earth metals and aluminum are often covered with an oxide film which hinders the reaction. 

The alkoxides of aluminum are polymeric with aluminum achieving four or six coordination. The adopted structure depends greatly on the bulkiness of the alkyl groups. For sterically large groups, for example, tertiary butyl, the preferred structure is a dimer (25). The isopropoxide, on the other hand, is trimeric (26) at elevated temperatures but tetrameric (27) at room temperature. ... 

Benzene has been alkylated by several series of secondary and tertiary alcohols in the presence of aluminum chloride. Ferric chloride is. recommended over aluminum chloride for alkylation by /-butyl alcohol. ... 

The reactivity of the aluminum-carbon bonds is greatly reduced in the 1 1 adducts, and this may be utilized in preparing particularly labile organoaluminum compounds which cannot be isolated in the free form. Thus tri-tert-alkyl alanes, such as tri-terf-butylalane, may be prepared as etherates from tertiary butyl lithium in diethylether (207) or from the corresponding magnesium tertiary alkyls (157, 159) ... 

Among the tertiary-butyl phenols, the o- and p-derivatives and 2,6-di-tert-butylphenol are commerically important. They are used in the production of antioxidants. o-tert-Butylphenol and 2,6-di-tert-butylphenol are produced by alkylation of phenol with isobutene at a reaction temperature of 100 °C in the presence of aluminum phenolate as catalyst. 

An alkyl group can replace a hydrogen atom of benzene in the Friedel-Crafis alkylation reaction. This reaction requires an alkyl halide, with an aluminum trihalide as the catalyst. The catalyst produces an electrophilic species, which may be a carbocation or a carbocation complexed with a counter ion. For simplicity in writing equations, we will show only the free carbocation. The reaction is commonly carried out only with alkyl bromides or alkyl chlorides. Aryl hahdes and vinyl halides do not react because the carbocations derived from these compounds do not form under usual reaction conditions. In contrast, tertiary carbocations, such as the ferr-butyl carbocation, readily form. 

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