Allyl bromide Aluminum chloride

Synonm Allyl Alcohol Allyl Bromide Allyl Chloride Allyl Chlorocarbonate Allyl Chloroformate Allylsilicone Trichloride Allyl Trichlorosilane Aluminum Chloride... 

Allylmagnesium bromide, 41, 49 reaction with acrolein, 41, 49 5-Allyl-l,2,3,4,5-pentachlorocyclopen-tadiene, 43, 92 Allyltriphenyltin, 41, 31 reaction with phenyllithium, 41, 30 Aluminum chloride, as catalyst, for isomerization, 42, 9 for nuclear bromination and chlorination of aromatic aldehydes and ketones, 40, 9 as Friedel-Crafts catalyst, 41, 1 Amidation, of aniline with maleic anhydride, 41, 93... 

Mediated by Tin. In 1983, Nokami et al. observed an acceleration of the reaction rate during the allylation of carbonyl compounds with diallyltin dibromide in ether through the addition of water to the reaction mixture.74 In one case, by the use of a 1 1 mixture of ether/water as solvent, benzaldehyde was allylated in 75% yield in 1.5 h, while the same reaction gave only less than 50% yield in a variety of other organic solvents such as ether, benzene, or ethyl acetate, even after a reaction time of 10 h. The reaction was equally successful with a combination of allyl bromide, tin metal, and a catalytic amount of hydrobromic acid. In the latter case, the addition of metallic aluminum powder or foil to the reaction mixture dramatically improved the yield of the product. The use of allyl chloride for such a reaction,... 

Later, Torii et al. found that the tin-aluminum-mediated allylation can be carried out with the less expensive allyl chloride, instead of allyl bromide, when a mixture of alcohol-water-acetic acid was used as the solvent.77 When combined with stoichiometric amounts of aluminum powder, both stoichiometric and catalytic amounts of tin are effective. As reported by Wu et al., higher temperatures can be used instead of aluminum powder.78 Under such a reaction condition, allyl quinones were obtained from 1,4-quinones, followed by oxidation with ferric chloride. Allylation reactions in water/organic solvent mixtures were also carried out electrochemically, with the advantage that the allyltin reagent could be recycled.79... 

This procedure is a modification of one described by Cortese.4 Allyl chloride is employed rather than allyl bromide because of its low cost. Biallyl has been prepared by the action of sodium 6 or aluminum 6 on allyl iodide from allyl mercuric iodide by dry distillation 7 or by the action of potassium cyanide solution 8 and by the action of magnesium on allyl bromide,4-9 on allyl chloride,4-10 on allyl iodide,11 or on 1,2,3-tribromopropane.12... 

Allyl alcohol, 26, 4 Allyl bromide, 25, 49 Allyl chloride, 24, 97 27, 7 Allyl cyanide, 24, 96, 97 Allyl ether, 26, 5 Allyl lactate, 26, 4 Alumina, activated, 23, 25 regeneration of, 23, 25 Aluminum, commercially pure (2S), 21, 9... 

In indium-mediated reactions, a catalytic use of expensive indium is desirable from an economical standpoint, and it has been achieved in combination with more electron-positive metals. Thus, allylation of aldehydes and ketones, as well as prenylation of 2-chlorobenzoquinone, has been performed by using metallic aluminum or zinc in combination with a catalytic amount of indium(m) chloride.63 Also, allylation of aldehydes and ketones with allyl bromide is carried out with a catalytic amount of indium powder (from 0.01 to 0.1 equiv.) in THF in the presence of manganese and chlorotrimethylsilane as the reducing and oxophilic agents, respectively (Scheme 2). 64,65... 

Allyl chloride or allyl bromide and dialkyl aluminum hydrides do not give halogenoalkyl alanes, the products being dialkyl aluminum monohalides and propene 270) ... 

Hence, monoprotection of 1,4-butanediol with Nall and trapping with allyl bromide led to 4-allyloxybutan-l-ol (Scheme 21). The crude product was treated with Jones reagent to furnish 4-allyloxybutyric acid (73). Treatment with oxalyl chloride in hexane at room temperature gave the corresponding acid chloride, which reacted with A-oxazoiidinone enolate to give a substrate for asymmetric alkylation upon treatment with NaHMDS and Mel. Reduction of 74 with lithium aluminum hydride led to a primary alcohol and recovered chiral auxiliary. Swern oxidation and treatment with Ph3PCHCOOMe afforded the a,P-unsaturatcd ester 75. 

Aluminum chloride allyl bromide Bromosilanes from silanes s. 19, 584... 

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