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  • 1
    Electronic Resource
    Electronic Resource
    Theoretical models for the reduction of arylmethyl halides by triorganotin hydridesPreliminary presentation of results at combined 45th Northwest-10th Rocky Mountain Regional Meeting of the American Chemical Society, Salt Lake City, UT, 13 June 1990. (1991)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 4 (1991), S. 485-491 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Two mechanistic pathways have been proposed for halogen atom transfer from the benzylic positions of halomethylarenes to triorganotin radicals. These are direct atom abstraction, which might involve an extremely polar transition state, and single electron transfer followed by bond cleavage. AM1 semi-empirical calculations have been utilized to model the rate-determining step of these processes. A wide range of related families of compounds have been studied, including substituted halomethylbenzes, selected halomethyl-substituted polycyclic aromatic hydrocarbons and oxygen- and nitrogen-containing chloromethyl-substituted heteroaromatic systems. Although these calculations are relatively simple, the present results corroborate the view that chlorine and bromine atom transfer from the benzylic position to triorganotin radicals involves a direct atom abstraction in the rate-determining step whereas reduction of the corresponding iodides proceeds via an electron-transfer mechanism.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610040804
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  • 2
    Electronic Resource
    Electronic Resource
    Differential photohydrodehalogenation reactivity of bromobenzenes (1,2,4-tribromobenzene, 1,2,3,5-tetrabromobenzene) and pentachlorobenzene: Sunlight-based remediation (1998)
    Chichester : Wiley-Blackwell
    Journal of Chemical Technology AND Biotechnology 72 (1998), S. 45-49 
    Details
    ISSN: 0268-2575
    Keywords: bromobenzene ; chlorobenzene ; dehalogenation ; photochemistry ; kinetics ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Notes: The photochemical dehalogenation of 1,2,4-tribromobenzene, 1,2,3,5-tetrabromobenzene and pentachlorobenzene in open-air solutions of acetonitrile using natural and artificial sunlight as the irradiation source has been investigated. The regiochemistry of mono-dehalogenation has been determined for 1,2,4-tribromobenzene and 1,2,3,5-tetrabromobenzene. Pentachlorobenzene did not react. 1,2,4-Tribromobenzene yielded three products, 1,4-dibromobenzene, 1,3-dibromobenzene and 1,2-dibromobenzene with isomer percentages of 52±1%, 39±2% and 9±1%, respectively. 1,2,3,5-Tetrabromobenzene yielded 1,3,5-tribromobenzene, 1,2,4-tribromobenzene and 1,2,3-tribromobenzene with relative product percentages of 60±2%, 29±2%, 11±1%. © 1998 SCI
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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