Allyl bromide Alumina

KF-alumina, allyl bromide, 80% yield. These conditions were developed because the typical strongly basic metal alkoxide-induced alkylation led to Beckmann fragmentation of the isoxazoline. 

Allyl bromide was purchased from Aldrich Chemical Company, Inc., and distilled from pulverized calcium hydride and filtered through basic alumina (10 g) immediately prior to use. 

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... 

Small amounts of water act in synergy with sonication and solid-support catalysis, for instance, in the reaction of thiocyanate ions. As in the previous case, presonication of the reagent and the support was found to improve the selectivity. These methods permit the substitution reactions to be run even in apolar solvents. Two practically simultaneous papers have described the preparation of aryl sulfones by alkylation of sodium arylsulfinates with reactive alkyl chlorides.i The reaction with benzyl chlorides is best performed on alumina, and allyl bromide reacts quantitatively in a DMF-water mixture in a few minutes. Activated primary halides undergo substitution by sodium azide in aqueous solution to give the potentially explosive organic azides. 1 The paper discusses the possible role of the relative densities of the starting material, the aqueous solution of the reagent, and the product in the success of the preparation. 

Sodium salts of carboxylic acids, including hindered acids such as mesitoic, rapidly react with primary and secondary bromides and iodides at room temperature in dipolar aprotic solvents, especially HMPA, to give high yields of carboxylic esters.679 The mechanism is Sn2. Another method uses phase transfer catalysis.680 With this method good yields of esters have been obtained from primary, secondary, benzylic, allylic, and phenacyl halides.681 In another procedure, which is applicable to long-chain primary halides, the dry carboxylate salt and the halide, impregnated on alumina as a solid support, are subjected to irradiation by microwaves in a commercial microwave oven.682 In still another method, carboxylic acids... 

Allyl chloride, 36, 63 Allylmagnesium bromide, 36, 61 Allylmagnesium chloride, 36, 63 Alumina, 34, 79, 35, 73 preparation for chromatography,... 

AUylbenzene, 86 Allyl benzoate, 26 Allyl chloride, 104 Allyl chloromethyl sulfide, 94 Allyl ethers, 246-247 Allylic alcohols, 150, 151-152, 328 Allylic chlorides, 151-152, 293 Allylic coupling, 211 Allylic hydroxylation, 246 Allylic oxidation, 35, 55-56, 171 2-Allylisopropyl bromide, 224 JT-Allylnickel bromide, 210 Allylphosphoric dichloride, 104 Alumina, 6... 

AlIylFp reagents [where Fp refers to the Fc(C,H5)(CO)2 residue] are examples of such reagents they are obtained by addition of the appropriate allyl chloride or tosylate to a solution of Fc(C5H5)(CO)2Na in THF at —78 "C. Chromatography on alumina allows isolation of the air-and heat-sensitive product in 80-95 % yield. In the presence of a./1-unsa turated ketones activated by an appropriate Lewis acid, cycloaddition provides stereoselectively the Fp-substituted cyclopenlane8. In the case of cyclohexenone as the acceptor, the two isomers formed in equal amounts both have a a. v-ring fusion. The Lewis acid of choice is freshly sublimed aluminum(III) bromide used in catalytic amounts (5 mol%). 

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