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  • 2,5-dialkylthiphenes  (1)
  • Diastereoselectivity  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Biodegradation 7 (1996), S. 313-327 
    ISSN: 1572-9729
    Keywords: bacteria ; 2,5-dialkylthiphenes ; petroleum ; sulfate ; 2,5-thiophenedicarboxylic acid ; thiophenes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Energy, Environment Protection, Nuclear Power Engineering , Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract 2,5-Dialkylthiophenes are found in bitumens and crude oils, and previous studies showed that bacterial metabolism of some with a methyl substituent lead to the formation of 5-methyl-2-thiophenecarboxylic acid, which persisted in the culture medium (Fedorak PM & Peakman TM 1992 Biodegradation 2: 223–236). The objectives of this investigation were to study the further metabolism of this acid, and of two dialkylthiophenes, 2,5-diundecylthiophene and 2-(3,7-dimethyloctyl)-5-methylthiophene. Undefined, oil-degrading mixed cultures were used. 5-Methyl-2-thiophenecarboxylic acid was oxidized to 2,5-thiophenedicarboxylic acid which was identified by gas chromatography-mass spectrometry (GC-MS). This dicarboxylic acid was degraded and supported the growth of a mixed microbial population, and approximately 50% of the sulfur in this substrate was detected as sulfate in the medium at the end of the 15-day incubation time. Mixed cultures were incubated with 2,5-diundecylthiophene or 2-(3,7-dimethyloctyl)-5-methylthiophene as their sole carbon source, and at various times some of these were freezedried and the residues were treated to form methyl esters of any carboxylic acids produced. GC-MS analyses showed the presence of several dicarboxylic acids, indicating that both alkyl groups were oxidized. A small amount of the dimethyl ester of 2,5-thiophenedicarboxylic acid was detected in the culture grown on 2,5-diundecylthiophene, and 37% of the sulfur from this dialkylthiophene was detected as sulfate in the medium after 35 days of incubation.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1434-193X
    Keywords: Indiumallyl compounds ; Vinylcyclopropanes ; α,β-Unsaturated carbonyl compounds ; Diastereoselectivity ; Dibenzylideneacetone ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---Allylindium reagents, prepared from excess allylic halide (Br or I) and indium metal, react with α,β-unsaturated ketones and aldehydes to give, after aerobic acidic workup, homoallyl-substituted vinylcyclopropanes. This process was explored and developed after a chance discovery arising from a side reaction in an attempted Pd-catalysed process. The structure of the cyclopropane arising from the reaction of bis(p-chlorobenzylidine)acetone was confirmed by X-ray crystallography. Whilst bis-α,β-unsaturated ketones give rise to a single homoallylcyclopropane species, α,β-unsaturated ketones and aldehydes give diastereomeric mixtures whose relative stereochemistry were assigned by NOE experiments. Crotylindium reagents react with good to perfect regioselectivity to afford tetrasubstituted cyclopropanes but prenylindium reagents fail to generate the analogous pentasubstituted rings.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
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