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  • 1
    Electronic Resource
    Electronic Resource
    Homolytic oxoalkylation of protonatedN-heteroaromatic compounds (1993)
    Springer
    Russian chemical bulletin 42 (1993), S. 1839-1843 
    Details
    ISSN: 1573-9171
    Keywords: homolytic oxoalkylation ; heteroaromatic bases ; lead tetraacetate ; manganese triacetate ; pyridine ; quinoline ; 1-methylcyclobutanol ; 1-methylcyclopentanol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The oxoalkylation of pyridine, 2-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethylpyridines, quinoline, 4-methylquinoline, isoquinoline, and pyrazine with oxoalkyl radicals generated from 1-methylcyclobutanol or 1-methylcyclopentanol under the action of Pb(OAc)4 or Mn(OAc)3 has been carried out. The reaction products are isomers with 2-(6)- and 4-positions of the oxoalkyl group in theN-heteroaromatic ring. The isomer ratios have been determined as a function of the structure of theN-heteroaromatic compound and the reaction conditions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00698999
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  • 2
    Electronic Resource
    Electronic Resource
    Electrochemical oxidative ring opening of 1-methylcyclobutanol (1996)
    Springer
    Russian chemical bulletin 45 (1996), S. 1246-1248 
    Details
    ISSN: 1573-9171
    Keywords: 1-methylcyclobutanol ; manganese(III) acetate ; electrochemical oxidation ; pentane-2-one ; 5-chloropentane-2-one ; β-cleavage
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The manganese(III) acetate-mediated electrooxidative ring opening of 1-methylcyclobutanol (1) in acetic acid affords pentane-2-one (2) as the major product. The reaction of 1-methylcyclobutanol with Mn(OAc)3-LiCl gives 5-chloropentane-2-one (4.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01431635
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  • 3
    Electronic Resource
    Electronic Resource
    Oxidation of 1-methylcyclobutanol by Pb(IV) and Mn(III) compounds (1992)
    Springer
    Russian chemical bulletin 41 (1992), S. 2189-2192 
    Details
    ISSN: 1573-9171
    Keywords: oxidation ; 1-methylcyclobutanol ; lead tetraacetate ; manganese triacetate ; β-cleavage
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The main product of the reaction of 1-methylcyclobutanol with Pb(OAc)4 in benzene is 1-phenyl-4-pentanone; the use of Mn(OAc)3 in acetic acid gives a mixture of 2,9-decanedione and methyl propyl ketone; 1-(chloro-, bromo-, thiocyano-, or cyano)-4-pentanone is formed in the presence of the systems Pb(OAc)4-metal halide or Mn(OAc)3-metal halide.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01150744
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  • 4
    Electronic Resource
    Electronic Resource
    Oxidation of 1-methyl- and 1-ethylcyclohexanol with cerium ammonium nitrate (1977)
    Springer
    Russian chemical bulletin 26 (1977), S. 1420-1424 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Conclusions 1. Cerium ammonium nitrate oxidizes 1-methyl- and 1-ethylcyclohexanol in aqueous acetonitrile in two directions, i. e., with elimination of the side alkyl group and with opening of the ring. 2. The oxoalkyl radicals formed during ring opening take part in hydrogen abstraction, rearrangement, recombination, and oxidation reactions. 3. During oxidation 1-methyl- and 1-ethylcyclohexanol partly react with acetonitrile by a earbonium ion mechanism to form N-(1-methylcyclohexyl)- and N-(1-ethylcyclohexyl)acetamide.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00928519
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  • 5
    Electronic Resource
    Electronic Resource
    Pb(OAc)4-Cu(OAc)2-mediated oxidation of 1-alkylcyclohexanols; β-decomposition of 1-alkylcycloalkoxy radicals (1984)
    Springer
    Russian chemical bulletin 33 (1984), S. 2490-2497 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Conclusions 1. The LTA-Cu(OAc)2-mediated oxidation of tertiary cyclic alcohols produces cycloalkoxy radicals (R=alkyl; n=4–5), which undergo Β-fragmentation along two pathways: a) with ring opening to generate oxoalkyl radicals RCO(CH2)n-1CH2, which are oxidized quantitatively to Ω-unsaturated ketones, and b) with elimination of alkyl radicals (R.) and the formation of cycloalkanones. This reaction forms the basis for the synthesis of Ω-unsaturated ketones. 2. The relative rates for the two pathways of Β-decomposition depend upon the structure of the alkyl substituent. The frequency of Β-fragmentation via ring cleavage increases as the stability of the departing radical (R.) decreases: $$\dot CH_3〈 RCH_2 \dot CH_2〈 CH_3 \dot CH_2〈 (CH_3 )_2 \dot CH〈 (CH_3 )_3 \dot C〈 C_6 H_5 CH_2$$ . 3. The oxidation of 1-alkylcyclohexanols in which the alkyl groups exceed four carbon atoms results in the formation of alkoxy radicals which undergo oxidative cyclization and are converted into 2-alkyl-5-pentamethylenetetrahydrofurans.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00960267
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  • 6
    Electronic Resource
    Electronic Resource
    Oxidation of methylcyclohexanols by the Pb(OAc)4-LiCl system (1986)
    Springer
    Russian chemical bulletin 35 (1986), S. 2256-2260 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Conclusion 1. In the reaction of 2-, 3-, and 4-methylcyclohexanols with the Pb(OAc)4,-LiCl oxidizing system, methylcyclohexylalkoxyl radicals are generated, and their formation was confirmed by EPR with the use of a spin trap. 2. The 2- and 4-methylcyclohexylalkoxyl radicals are regioselectively rearranged into 1-methyl- and 3-methyl-5-formylamyl radicals, and the 3-methylcyclohexylalkoxyl radical decomposes in two directions, yielding 2-methyl- and 4-methyl-5-forraylarayl radicals. In the Pb(OAc)4-LiCl system, these radicals are quantitatively oxidized into chloroalkanals. 3. The trans-2 and cis-3-methylcyclohexanols exhibit higher reactivity with respect to the Pb(OAc)4-LiCl system than cis-2 and trans-3-methylcyclohexanols. The reactivity of both isomers of 4-methylcyclohexanol is the same.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00953334
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  • 7
    Electronic Resource
    Electronic Resource
    Reaction of aromatic hydrocarbons with cerium ammonium nitrate (1975)
    Springer
    Russian chemical bulletin 24 (1975), S. 1328-1329 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Conclusions 1. The reaction of benzene and naphthalene with an equimolar amount of cerium ammonium nitrate respectively gives nitrobenzene and 1-nitronaphthalene. Anthracene under similar conditions is converted to anthraquinone and 9-nitroanthracene (3∶1). 2. Nitrobenzene is oxidized by cerium ammonium nitrate to 1,3-dinitrobenzene, 1-nitronaphthalene is oxidized to 1,4-naphthoquinone, and 9-anthracene is oxidized to anthraquinone.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00922077
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  • 8
    Electronic Resource
    Electronic Resource
    Oxidation of cyclohexene with Ce (IV) salts (1977)
    Springer
    Russian chemical bulletin 26 (1977), S. 1534-1536 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Conclusions Together with the main products, namely cyclohexen-2-ol and cyclohexen-2-one, the oxidation of cyclo-hexene with cerium ammonium nitrate or cerium ammonium sulfate gives cyclohexanol and cyclohexanone, which are probably formed by the cation-radical mechanism.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00928553
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  • 9
    Electronic Resource
    Electronic Resource
    Oxidative cleavage of 1-alkylcycloalkanols by Pb(IV) acetate-Ag(I) acetate system (1981)
    Springer
    Russian chemical bulletin 30 (1981), S. 931-933 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Conclusions 1. The oxidation of 1-alkylcyclopentanols and 1-alkylcyclohexanols by the Pb(OAc)4- AgOAc system leads to the generation of 5- and 6-oxoalkyl radicals, which mainly recombine with each other to give diketones. 2. Straight-chain diketones RCO(CH2)8COR are obtained from the 5-oxoalkyl radicals, and branched diketones RCOCH(C24H9)CH(C4H9)COR are obtained from the 6-oxoalkyl radicals. Rearrangement, with the 1,5-transfer of hydrogen, of the 6-oxoalkyl radicals to the 1-oxoalkyl radicals precedes the formation of the branched diketones.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00955326
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  • 10
    Electronic Resource
    Electronic Resource
    Oxidative δ-chlorination of aliphatic alcohols (1986)
    Springer
    Russian chemical bulletin 35 (1986), S. 1540-1540 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00954851
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