TY - JOUR AB - Direct injection Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS), and ultra-high performance liquid chromatography coupled to mass spectrometry (UPLC/MS) were combined for the non-targeted analysis of wine metabolites. The unrivalled resolution on mass measurement allowed by the former and the separation ability of isomeric and isobaric substances by the latter, clearly increases the scope of detectable unknown metabolites in wines. Such methodology is illustrated through the comparison of chemical spaces of a young and an older Pinot noir wine. RP and HILIC chromatography could reveal up to five isomers for a given mass, throughout the explored mass range. CHO, CHOS and CHONS chemical spaces exhibited higher diversities in the older wine, illustrating a molecular oeno-diagenesis process during wine ageing, whereas nitrogen-containing compounds (CHON chemical space) appeared to be fewer in the older wine, likely due to precipitation. This methodological combination is a promising contribution to the wine metabolomics toolkit. AU - Roullier-Gall, C. AU - Witting, M. AU - Tziotis, D. AU - Ruf, A. AU - Gougeon, R.* AU - Schmitt-Kopplin, P. C1 - 43963 C2 - 36714 CY - Oxford SP - 2983-2990 TI - Integrating analytical resolutions in non-targeted wine metabolomics. JO - Tetrahedron VL - 71 IS - 20 PB - Pergamon-elsevier Science Ltd PY - 2015 SN - 0040-4020 ER - TY - JOUR AB - Six cyclic stilbene derivatives with hindered free rotation around the C(vinyl) C(phenyl) single bond were synthesized by McMurry coupling. The torsion angles around the double and the single bond, and the C=C bond length were obtained for many of the compounds from their solid-state structures. The photochemical isomerization was subsequently investigated for all derivatives under various conditions. The parent 1-(1-tetralinylidene)tetralin underwent efficient oxidative electrocyclization. The 2,2,2',2'-tetramethylated analogue was resistant towards photooxidation, however, its cis-isomer thermally re-isomerized to the more stable trans-isomer. AU - Oelgemöller, M.* AU - Frank, R. AU - Lemmen, P.* AU - Lenoir, D. AU - Lex, J.* AU - Inoue, Y.* C1 - 8030 C2 - 29965 SP - 4048-4056 TI - Synthesis, structural characterization and photoisomerization of cyclic stilbenes. JO - Tetrahedron VL - 68 IS - 21 PB - Pergamon-Elsevier PY - 2012 SN - 0040-4020 ER - TY - JOUR AU - Schulz, A.* AU - Adermann, K.* AU - Eulitz, M. AU - Feller, S.M.* AU - Kardinal, C.* C1 - 21406 C2 - 19523 SP - 3889-3891 TI - Preparation of Disulfide-Bonded Polypeptide Heterodimers by Titration of Thio-Activated Peptides with Thiol-Containing Peptides. JO - Tetrahedron VL - 56 PY - 2000 SN - 0040-4020 ER - TY - JOUR AB - Contrary to a previous report, there is no solvent-dependent selectivity to either of the double-bond-dechlorinated derivatives when Bromodan is irradiated in hexane or methanol. The 7-dechlorinated derivative formed on photolysis in triethyl amine is debrominated on further irradiation. 13C chemical shifts and long-range CH coupling constants indicate that the structural assignment of the double-bond-dechlorinated isomers must be reversed. AU - Turner, W.V. AU - Gäb, S. C1 - 17650 C2 - 10565 SP - 3711-3716 TI - Another look at the photodechlorination of bromodan. JO - Tetrahedron VL - 45 IS - 12 PY - 1989 SN - 0040-4020 ER - TY - JOUR AB - The preparation of thirteen halo- and methyl-substituted 3,5-cyclohexadiene-1, 2-diol-1'carboxylic acids from microbial oxidation of the corresponding benzoic acids is reported. The properties, including CD-, UV-, MS-spectra are compared. The cis-configuration of the glycol group is determined by acetonide formation with 2,2-dimethoxypropane and from spectroscopic data. AU - Reineke, W. AU - Otting, W.* AU - Knackmuß, H.J. C1 - 41420 C2 - 38176 SP - 1707-1714 TI - cis-Dihydrodiols microbially produced from halo- and methylbenzoic acids. JO - Tetrahedron VL - 34 IS - 11 PY - 1978 SN - 0040-4020 ER - TY - JOUR AB - Two extensive mechanisms are proposed for cyclotrimerization of nitriles to s-triazines under high pressure. The availability of these mechanisms is proven by synthesis of some new symmetrically substituted s-triazines; simultaneously, however, their limits are demonstrated. Furthermore, there were found rearrangement and cyclic degradation reactions as reaction possibilities for s-triazines under high pressure. Both reactions are based on an equilibrium in alcohol between symmetrically substituted s-triazine and iminoether. AU - Jarre, W. AU - Bieniek, D. AU - Korte, F. C1 - 42408 C2 - 38441 SP - 619-623 TI - Synthese und reaktionen von symmetrisch substituierten s-Triazinen unter hohem druck. Hochdruckreaktionen, 8. Mitteilung. JO - Tetrahedron VL - 31 IS - 6 PY - 1975 SN - 0040-4020 ER - TY - JOUR AB - Dicarboxylic acid (1) and its dimethylester (2) respectively were irradiated in solutions and in gaseous phase by UV-light of a high pressure mercury lamp with emission above 230 nm. Immersion wells of pyrex and quartz were used for the irradiation experiments. After an irradiation with UV-light having long wavelengths (λ > 300 nm), followed by a diazomethane treatment of the reaction mixture, compounds 5-11 could be isolated from solutions of the dicarboxylic acid (1) in acetone. Dimethylester (2) revealed comparable results. Compounds 3 and 4 were obtained by irradiating the dimethylester (2) in n-hexane and water/methanol respectively with wave-lengths below 300 nm. The dimethylester (2) gaseously distributed in air, yielded two isomeric products and a dechlorination product by irradiation with UV-light (λ < 300 nm). The bridged compound 5 is one of the isomeric photoproducts. This contribution mainly consists in the structural elucidation of products being formed under the influence of UV-light. The spectroscopical data of compounds 1-11 resulting in the proposed structures given in Fig 1 are discussed in the following text. AU - Gäb, S. AU - Parlar, H.A. AU - Korte, F. C1 - 42662 C2 - 35521 SP - 1145-1151 TI - Beiträge zur ökologischen Chemie LXI : Photoreaktionen des Aldrin/Dieldrin-Metaboliten Dihydrochlordendicarbonsäure (4,5,6,7,8,8-Hexachloro-4,7-Methano-3a,4,7,7a-Tetrahydroindan-1,3-Dicarbonsäure). JO - Tetrahedron VL - 30 IS - 9 PY - 1974 SN - 0040-4020 ER - TY - JOUR AB - Bei der Bestrahlung von DDE (1) in n-Hexan mit UV-Licht verschiedener Wellen-längen entstehen neben den bekannten Photoprodukten II und III ein Photoisomerisationsprodukt (IV) und zwei weitere Substanzen aus der Reaktion mit dem Lösungsmittel (V und VI). In Dioxan-Wasser und als Festkörper entstehen II, III und IV bei der Bestrahlung in Aceton, bei Zugabe katalytischer Mengen von Bleiacetat zu der Dioxan-Wasser-Mischung entstehen zusätzlich zwei nicht identifizierte Photoprodukte. Bei UV-Bestrahlung von DDE in der Gasphase konnten nur die Verbindungen III und IV nachgewiesen werden. AU - Kerner, I. AU - Klein, W. AU - Korte, F. C1 - 42656 C2 - 37915 SP - 1575-1578 TI - Beiträge zur ökologischen chemie-XXXIII. Photochemische reaktionen von 1,1-dichlor-2(p,p′-dichlorphenyl)äthylen (DDE). JO - Tetrahedron VL - 28 IS - 6 PY - 1972 SN - 0040-4020 ER - TY - JOUR AB - The compounds III-VII were isolated from solutions of dieldrin (I) and nitrogen tetroxide in fluorocarbon after irradiation with UV-light having long wavelengths (λ s $ ̌300 nm). Irradiation of solutions of dieldrin and nitrogen tetroxide in carbon tetrachloride under similar conditions yielded compounds II-VI. Compound IV was detected after irradiation of a solution of dieldrin and ozone in fluorocarbon. In the presence of nitrogen dioxide dieldrin distributed in nitrogen in gaseous state was converted mainly into photodieldrin (IX) by UV-light. Irradiation of dieldrin gaseously distributed in ozonized air yielded, as in ozonic solution, several products of higher molecular weight, which, however, were not isolated. Compound VIII, excreted in the urine of rats to which dieldrin was administered,2 was obtained by dehydrochlorination of compound VI. Thus the structure of the metabolite3 could be confirmed by means of a NMR- and UV-spectrum of compound VI. The spectra of compounds II-VII are discussed, from which the proposed structures given in Fig 1 are derived. Radical mechanisms are proposed for these reactions. AU - Nagl, H.G. AU - Korte, F. C1 - 42641 C2 - 37916 SP - 5445-5458 TI - Beiträge zur ökologischen chemie-XLVIII. Reaktionen von dieldrin mit stickstoffdioxyd und ozon in ultraviolettem Licht. JO - Tetrahedron VL - 28 IS - 21 PY - 1972 SN - 0040-4020 ER - TY - JOUR AB - Bei Bestrahlung von Dieldrin (I) in n-Hexan oder Methanol/Wasser mit UV-Licht verschiedener Wellenlänge entstehen drei bisher unhekannte unverbrückte bzw. verbrückte Dechlorierungsprodukte neben den bekannten Photoprodukten des Dieldrins, die durch Variation der Bestrahlungsbedingungen präparativ herstellbar sind (IV-VI). Bei Bestrahlung in der Gasphase entsteht unter den bisher benutzten Bedingungen, wie erwartet, lediglich das bekannte Isomerisierungsprodukt Photodieldrin (II). AU - Nagl, H.G. AU - Klein, W. AU - Korte, F. C1 - 41128 C2 - 37927 SP - 5319-5325 TI - Beiträge zur ökologischen Chemie-XXVIII. Über das Reaktionsverhalten von Dieldrin in Lösung und in der Gasphase. JO - Tetrahedron VL - 26 IS - 22 PY - 1970 SN - 0040-4020 ER -