Substitution reactions involving organoaluminum compounds Communication 4. Synthesis of alkyl-substituted cyclopropanes via the alkylation of homoallylic alcohol tosylates with trialkylalanes

Conclusions A method for the synthesis of alkyl-substituted cyclopropanes via the reaction of homoallylic alcohol tosylates with trialkylalanes is described.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1109–1114, May, 1985.For communication No. 3, see [1].     

Substitution reactions with the participation of organoaluminum compounds. 7. Reaction of organoaluminum compounds with monochlorodimethyl ether

Conclusions The reaction of monochlorodimethyl ether with different organoaluminum compounds is only a convenient method for the isolation of alkyl methyl ethers in the case of trialkylalanes.For previous communication 6, see [12].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 425–428, February, 1988.     

Application of hydroalumination reactions in organic syntheses. coupling reactions of organoaluminum compounds with allylic halides catalyzed by copper compounds

Hydroalumination of olefins with lithium aluminum hydride followed by treatment with various allylic halides in presence of a catalytic amount of copper(I) chloride resulted in coupling. This new development provides a simple operational method for lengthening the carbon chain of olefins.     

Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols

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An effective synthesis method for secondary fluorinated alcohols via the reaction of esters of polyfluorinated acids with trialkylalanes

Unlike nonfluorinated analogs, complex esters of polyfluorinated acids in reactions with trialkylalanes produce only polyfluorinated secondary alcohols.Department of Fine Organic Synthesis, Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, 450054 Ufa. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 10, pp. 2339–2341, October, 1992.     

Aqueous electrosynthesis of carbonyl compounds and the corresponding homoallylic alcohols in a divided cell

An aqueous paired electrosynthesis is studied in a divided cell. On graphite anode Br⁻ was oxidized to Br₂ and this generated Br₂ oxidized alcohols to the corresponding carbonyl compounds while Sn²⁺ was reduced to Sn⁰ on graphite cathode. Then the produced metallic tin mediated allylation of the carbonyl compounds with allyl bromide to generate the corresponding homoallylic alcohols. In the reaction the mediators (Sn and Br₂) were generated in situ and could be reused via the electrolysis. Both working electrode and the counter electrode were utilized to generate useful products without the sacrifice of the electrode materials.     

Organosilicon compounds of the furan series VIII. Reaction of triethylsilane with unsaturated alcohols

When triethylsilane is reacted with unsaturated primary alcohols such as allyl, cinnamic, and furylallyl alcohols, in the presence of H₂PtCl₆, the main reaction is one of dehydrocondensation. With secondary unsaturated alcohols such as methylallylcarbinol and furylallylcarbinol, dehydrocondensation and hydrosilylation take place simultaneously. A number of new furylalkoxy- and furyl-alkenoxysilanes are synthesized and described.     

Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes

[reaction: see text] Acid-catalyzed nucleophilic substitution of bicyclic hydrazine-epoxide involves nitrogen participation, leading to a skeletal rearrangement. This transformation enables the fast preparation of disubstituted bicyclic hydrazines in a regio- and stereoselective manner, leading to several polyfunctional diaminocyclopentanes after hydrogenolysis.     

Substitution of the halogen atoms in α-halogenonitro compounds of the aliphatic series 4. Interaction of carbonyl compounds with ethyl chloronitroacetate under the conditions of the Reformatsky reaction

The reaction of ethyl chloronitroacetate with carbonyl compounds of the aliphatic series under the conditions of the Reformatsky reaction in ether, THF, or benzene does not proceed with the substitution of the chlorine atom, but by the scheme of the Anri reaction with the formation of ethyl -nitro--chloro--hydroxycarboxylates. The reaction proceeds via the intermediate formation of the zinc salt of ethyl chloronitroacetate.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2729–2732, December, 1989.