Ethylaluminium chloride

Friedel-Crafts alkylation of benzene or toluene by allyl chloride in presence of ethylaluminium chlorides is vigorous even at — 70°C, and explosions have occurred. See Lewis acids, etc., next below... 

Treatment of 2,3 Cpoxy-l-amines with Lewis acid induces a rearrangement to aziridinium ions that react efficiently with a nucleophiles to give functionalized hydroxy sulfides or hydroxy amines (Equation 23) <1997SL11>. Under the influence of ethylaluminium chloride, an epoxide tethered to an azide undergoes Lewis acid-assisted cyclization followed by an intramolecular Schmidt reaction and subsequent in situ reduction of the intermediate iminium species upon addition of sodium borohydride (Scheme 8). This protocol was used as a key step in a novel synthesis of indolizidine alkaloids of pharmaceutical interest <20030L583, 2004JOC3093>. 

Kennedy and coworkers improved considerably the degree of grafting by using di-ethylaluminium chloride at low temperature and claimed that this achievement was due to the essential absence of transfer reactions in the branching pdymerisation. The work of this prolific group has recently been the object of an entire issue of Applied Polymer Symposium and the interested reader will find in those papers a general introduction to cationic grafting and the ecific contributions and applications achieved at Akron. 

E.s.r. (at room and glass temperatures) and u.v. spectroscopic studies on mixtures of dichlorobis(Ti-cyclopentadienyl)vanadium and ethylaluminium chloride indicate that a number of species are formed, some of which are active catalysts for ethylene polymerization. The most detailed results were obtained for (the catalytically inactive) species (72). ... 

It has been reported recently that organotitanium compounds prepared conveniently from the corresponding Grignard reagents and titanocene chloride cyclize with an appropriately positioned internal alkene in the presence of ethylaluminium chloride (equation 119) ... 

The catalyst may be homogeneous or heterogeneous. The former usually consists of a transition metal compound such as tungsten hexachloride with a Lewis acid or organometallic compound such as ethylaluminium chloride, tetramethyl or tetrabutyltin, or triethylboron. Heterogeneous catalysts are usually oxides or carbonyls of molybdenum or tungsten on alumina or silica. 

In 2008, the Feng group reported highly enantioselective Pudovik reaction of diallq lphosphites to aldehydes with chiral tridentate Schiff base 52-di-ethylaluminium chloride complex as the catalyst (Scheme 19.60). A broad... 

Table 5.3-3 Solubilities of 1-butene and M-butane in the acidic mixture composed of l-butyl-3-methylimida-zolium ([BMIM]) chloride/alumini-um chloride/ ethylaluminium dichloride (1 1.22 0.06 molar ratio) as a function of temperature under atmospheric pressure.

The ethylaluminium dichloride-catalyzed reaction of p-toluenesulphinyl chloride with alkenes 136 successfully applied191 for the synthesis of allylic sulphoxides 137 (equation 74) may also be regarded formally as a reaction of sulphinyl chlorides with compounds containing active hydrogen atom. Treatment of an alkene 136 with one equivalent each of ethylaluminium dichloride and p-toluenesulphinyl chloride at room temperature gave the corresponding 137. This reaction is very general and proceeds in... 

Interaction produces distillable ethylaluminium azide chloride, but the residue is explosive. 

Diethylaluminium bromide, 1670 Diethylaluminium chloride, 1671 Diisobutylaluminium chloride, 3064 Dimethylaluminium bromide, 0882 Dimethylaluminium chloride, 0883 Ethylaluminium bromide iodide, 0841 Ethylaluminium dibromide, 0842 Ethylaluminium dichloride, 0843 Ethylaluminium diiodide, 0844 Hexaethyltrialmninimn trithiocyanate, 3695 Methylaluminium diiodide, 0423 Triethyldialuminium trichloride, 2556 Trimethyldialuminium trichloride, 2556 See Other ALKYLMETAL HALIDES... 

Diethylaluminium bromide, 1664 Diethylaluminium chloride, 1665 Diisobutylaluminium chloride, 3059 Dimethylaluminium bromide, 0878 Dimethylaluminium chloride, 0879 Ethylaluminium bromide iodide, 0837 Ethylaluminium dibromide, 0838 Ethylaluminium dichloride, 0839 Ethylaluminium diiodide, 0840 Hexaethyltrialuminium trithiocyanate, 3688 Methylaluminium diiodide, 0422 Triethyldialuminium trichloride, 2551 Trimethyldialuminium trichloride, 1288 See ALKYLALUMINIUM DERIVATIVES (references 1,2)... 

Selective C-S bond cleavage of a /3-sultam ring bearing a variety of substituents at C-3 and C-4 can be achieved by reaction with Lewis acids and yields aryl ketones or aldehydes. A solution of ethylaluminium dichloride in hexane is easier to handle than solid aluminium chloride due to their relative moisture sensitivities (Scheme 25) <1998T8941>. 

Diethylaluminium chloride Ethylaluminium dichioride Hydrocarbons, halogenated Hydrocarbons, halogenated Moderate, useful for proton-sensitive reactions Moderate, useful for proton-sensitive reactions... 

In an interesting application of aluminacyclopentanes 44, the tetrahydrothiophenes 45 were synthesized employing a reaction with thionyl chloride. The starting compounds were readily prepared from the alkenes 46 and ethylaluminium dichloride in the presence of a zirconium catalyst. A mechanistic rationale for the formation of 45 was also provided <04T1281>. 

Metal halides include the metal alkyl halide ethylaluminium ses-quichloride and the metal aryl halide phenylmagnesium chloride both... 

Treatment of olefins with toluenesulphinyl chloride and ethylaluminium dichloride in ether at room temperature gives allylic sulphoxides via a formal ene reaction (Scheme 57)/ The Lewis acid acts both as a catalyst for the rearrangement and as a proton scavenger, reacting with the hydrogen chloride produced to give ethane and aluminium chloride. 

Reaction of cyclo-octa-1,3-diene with ethylene in the presence of a catalyst prepared from n-allylnickel chloride, ethylaluminium sesquichloride, and a chiral phosphane can give 3-vinylcyclo-octane of up to 70 % optical purity. Alkylsulphonium salts are obtained from the reaction of thioethers with protonated alkenes thus cyclo-octa-1,3-diene gives (315) and cyclododeca-... 

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