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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 338 (1996), S. 179-181 
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonides of Isomeric Octalins by Dry Ozonolysis on Polyethylene
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 340 (1998), S. 733-737 
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: L-Malic acid (2) reacts with trifluoroacetic anhydride under anhydrous conditions to give (S)-trifluoroacetoxy-succinic acid anhydride (3). The anhydride 3 undergoes regioselective ring opening with an excess of anilines or primary aliphatic amines leading to N-substituted-(S)-3-hydroxy-succinamic acids (4a-g). Structural elucidation of the reaction products 4a-g was based on analytical and spectroscopic data and on an X-ray structure analysis of 4b. Secondary aliphatic amines react with 3 by condensation and subsequent elimination to furnish N,N′-disubstituted fumaric acid amides 5a, b. Some N-substituted-2-hydroxysuccinamic acids (7a,b) were also prepared for spectral comparison with the 3-hydroxy compounds.
    Additional Material: 1 Ill.
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1993-1999 
    ISSN: 0947-3440
    Keywords: Ozonides ; Cycloolefins ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonolyses in pentane of the unsubstituted cycloolefins having eleven-, twelve-, fourteen- and sixteen-membered rings (1b-e) and of cyclohexadecen-8-one (12) gave the corresponding cis- (2b-e; cis-15a) and trans-ozonides (3b-e; trans-15a), whereas cyclodecene (1a) gave only the corresponding cis-ozonide (2a). Ozonolyses on polyethylene of the dimethyl-substituted cycloolefins bearing fourteen- and sixteen-membered rings (7b, c) also afforded cis- and trans-isomeric ozonides (8, 9), whereas from the twelve-membered ring (7a) only the corresponding cis-ozonide (8a) was formed.
    Additional Material: 3 Ill.
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Advanced Materials 8 (1996), S. 381-384 
    ISSN: 0935-9648
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Additional Material: 1 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 2189-2194 
    ISSN: 0947-3440
    Keywords: Nitroxide radicals ; 2,5-Dihydroimidazoles ; Hydroxylamines, secondary ; α-Keto hydroxylamines ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of functionalized 2,5-dihydro-1-hydroxy-2-R1-2-R2-4-R3-imidazoles were prepared by cyclocondensation of α-oxo hydroxylamines with ketones R1R2C = O in the presence of ammonia (R1 = R2 = 2-pyridyl, 4,5-diazafluoren-9-ylene, R3 = Me; R1 = CH2OCOMe, CH2OCOPh, 2-thienyl, CH2OH, CO2K, R2 = R3 = Me; R1 = Py, R2 = Me, R3 = Ph; R1 = R2 = CH2OCOPh, CH2OH, R3 = Me) and oxidized to the corresponding nitroxide radicals. The structures of 2′,5′-dihydro-1′-hydroxy-4′,5′,5′-trimethylspiro[4,5-diazafluoren-9,2′-imidazole] (2) and of 2-(acetoxymethyl)-2,5-dihydro-2,4,5,5-tetramethylimidazole-1-oxyl (14) were determined by X-ray diffraction. In the crystal 2 forms one-dimensional chains through hydrogen bonding between N atoms of the hydroxylamine and imidazoline groups.
    Additional Material: 1 Tab.
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  • 6
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 503-510 
    ISSN: 0899-0042
    Keywords: enantioseparations ; carrageenans ; sulfated polysaccharides ; beta blockers ; tryptophan and derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lambda-carrageenan, a linear high molecular weight sulfated polysaccharide, has been employed as a chiral selector in capillary electrophoresis for the separation of enantiomers of weakly basic pharmaceutical compounds. The racemic compounds that were enantioresolved included propranolol, pindolol, tryptophanol, laudanosine and laudanosoline. In addition, the diastereomeric pair of cinchonine and cinchonidine were also resolved. Method conditions such as buffer pH, electrolyte concentration, column temperature, and chiral selector concentration were found to be important for improvement of enantioselectivity. © 1996 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
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  • 7
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 229-237 
    ISSN: 0899-0042
    Keywords: deuterium labelling ; menthocitronellol ; citronellol ; enantioselective multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS) ; dynamic headspace analysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanistic aspects of the biogenesis of the chiral monoterpenoid rose oxide in Pelargonium graveolens L'Héritier are investigated using deuterium-labelled precursors. After administration of the precursors using the cut-stem method, the dynamic headspace extracts of the plants are analysed using multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS). It is unequivocally shown that this plant is able to convert citronellol and menthocitronellol into cis-/trans-rose oxide. Menthocitronellol is converted into rose oxide with a clearly detectable enantiodiscrimination. These facts may be explained with the presence of an oxidase, which is able to oxidize citronellol and menthocitronellol in allylic position. A photooxygenation mechanism including singlet oxygen as the oxidizing agent is rather unlikely. Chirality 10:229-237, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
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  • 8
    ISSN: 0006-3592
    Keywords: halogenated compounds ; basidiomycetes ; Bjerkander adusta ; flavors ; membrane inlet mass spectrometry (MIMS) ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: Membrane inlet mass spectrometry has been used for the characterization of halogenated organic compounds produced by the fungus Bjerkandera adusta. Using this technique we obtained electron impact-, chemical ionization-, electron capture negative chemical ionization-mass spectra and tandem mass spectra directly from the growth medium. Through this direct analysis of the samples we identified novel bioconversion products and confirmed recently published data on the production of both chlorinated and brominated methoxybenzaldehyde metabolites. Growth profiles of the culture grown on a defined medium showed that the production of secondary metabolites starts after approximately 6 days and reaches maximal concentrations of 25-250 μM after 15-20 days. Although delayed, the production of secondary metabolites paralleled a depletion of glucose from the medium and stopped shortly after all glucose had been consumed. Experiments in which fluoro- and bromo-labeled 4-methoxybenzaldehydes were added to the medium at day 8 showed biotransformation of these compounds into chloro-3-fluoro-4-methoxy-benzaldehyde and chloro-3-bromo-4-methoxybenzaldehyde, respectively. No dichlorinated products were observed, suggesting that halogenation takes place only at the meta position on the 4-methoxybenzaldehydes. These experiments are the first to bring direct evidence of a halogenation mechanism, where the enzymatic attack takes place directly on the 4-methoxybenzaldehyde intermediates. © John Wiley & Sons, Inc.
    Additional Material: 9 Ill.
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  • 9
    ISSN: 0947-5117
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
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  • 10
    ISSN: 0947-6539
    Keywords: enzyme inhibitors ; niobium complexes ; peptide aldehydes ; pinacol coupling ; vanadium complexes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Peptide aldehydes 15 a-c are prepared without epimerization from enantiomerically pure (S)-α-amino acids (Scheme 3). Reductive pinacol homocoupling of 15 a-c, induced by vanadium complex 11 or niobium complex 16 in refluxing THF, yields C2-symmetrical (S,R,R,S)-configurated 6a, 6b and 2, respectively, with moderate to high stereoselectivity (Scheme 4). In a novel protocol for the preparation and utilization of THF solutions of 11, the isolation of air-sensitive intermediates can be avoided and the potent HIV protease inhibitor 2 prepared in enantio- and diastereomerically pure form on a kilogram scale without chromatographic purification. The (S,R,R,S) selectivity of the pinacol homocouplings is confirmed by means of an independent, stereochemically unequivocal synthesis of 6 a and 2 from D-mannitol 4 (Scheme 1).
    Additional Material: 1 Tab.
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