Universität Stuttgart
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Item Open Access Darstellung von Didehydropyridinen aus (Trimethylsilyl)pyridinen(1991) Effenberger, Franz; Daub, WolfgangHalogen-substituted (trimethylsilyl)pyridines 2, 3, 5 - 7 and trifluoromethylsulfonyloxy-substituted (trimethylsilyl)pyridines 9b, 11b are obtained from 2- and 3-halopyridines 1, 4 or hydroxypyridines 8, 10, and 12. Reactions of the 3- and 2-(trimethylsilyl)pyridines 2,9b and 11b with bases in the presence of furans 15 give only protodesilylation or hydrolysis products but no indication is found for the formation of a 2,3-didehydropyridine. 3-Bromo-4-(trimethylsilyl)pyridine (5a) reacts with KOCMe3 in the presence of furan (15a) to give a mixture of products from which the isoquinoline derivative 20 and the tert-butoxypyridines 23, 24 are formed by addition to 3,4-didehydropyridine. Under comparable conditions far higher yields of 3,4-didehydropyridines are obtained by treatment of the 3-halo-2,4-bis(trimethylsilyl)pyridines 7 with strong bases.Item Open Access Electrooptical investigation on the three switching states of a chiral smectic side group polymer(1992) Gießelmann, Frank; Zugenmaier, Peter; Scherowsky, Günter; Kühnpast, Kurt; Springer, JürgenElectrooptical properties of a polyacrylate with 1,3-dioxolane-4-carboxylic acid as chiral building block terminally attached to phenylpyridine mesogenic moiety and linked via a C11 spacer were studied. Results showed that the formation of 3 switching states for the polymer occurred upon conformational interactions between the side groups and the main chain.Item Open Access Neutronenbeugungsuntersuchungen an fluiden Systemen(1996) Pfleiderer, TillIm Rahmen dieser Arbeit wurden Hochdruckneutronenbeugungsexperimente an einer fluiden Mischung der deuterierten Alkane Methan (67 Molprozent) und Ethan (33.3 Molprozent) bei einer Temperatur von 370 K ausgewertet. Nach Korrekturen auf Mehrfachstreuung, Absorption sowie inelastischen Effekten wurden die Strukturfaktoren dieser Mischung bei sechs verschieden ueberkritischen thermodynamischen Zustaenden ermittelt. Diese Strukturfaktoren wurden in ihre intra- und intermolekularen Anteile separiert, wobei die Molekuelstrukturen von Methan und Ethan bestimmt werden konnten. Abschliessend wurden die intermolekularen Anteile der Strukturfaktoren mit Hilfe einer Fouriertransformation in die intermolekularen Anteile der Summe der gewichteten Atompaarkorrelationsfunktionen ueberfuehrt.Item Open Access Electric field induced domain formation in surface stabilized ferroelectric liquid crystal cells(1994) Dierking, Ingo; Gießelmann, Frank; Schacht, Jochen; Zugenmaier, PeterTwo types of domains have been observed for S sub(C) ferroelectric liquid crystals in surface stabilized cells (SSFLC) by application of a high electric field with the smectic layers tilted by the amount of the chevron angle with respect to the normal of the rubbing direction in the substrate plane. The layer structure resembles that of a chevron configuration in the plane of the substrate similar to the recently reported stripe-shaped SSFLC structure. The two domain types 'appear' to switch in a reciprocal fashion when applying an AC electric field and observed between crossed polarizers. The temperature dependence of this effect has been investigated and an explanation proposed analogous to a striped texture model.Item Open Access Diastereoselective synthesis of α-Hydroxy- and α-amino-indolizidines and -quinolizidines : evidence for a novel cyclization/hydride migration mechanism in the TiCl4-induced reaction of prolinalbenzylimines by deuterium labeling studies(1994) Laschat, Sabine; Grehl, MatthiasLewis acid-catalyzed cyclization of prolinal and 2-piperidine-carbaldehyde benzylimines 11, 12 results in the diastereoselective formation of α-amino-β-alkyl-substituted indolizidines 15, 17, 19, 21 and -quinolizidines 16, 18, 20, respectively. Both diastereoselectivity and constitution depend on the Lewis acid. FeCl3 yields α,β- trans-α-(benzylamino)-β-isopropenyl derivatives 15 and 16, probably by a cationic cyclization via carbenium ions 32a, b. In contrast, TiCl4 yields ,α,β- cis-α-(benzylideneamino)-β-isopropyl derivatives 19 and 20 by a novel cyclization/intermolecular hydride transfer mechanism, which was supported by deuterium labeling studies. Compounds 15, 16, 19, and 20 were converted to the diastereomeric acetamides 24, 25 and 28, 29. By an analogous cyclization of the aldehydes 8 and 9 only α ,β-cis-α-hydroxy--isopropenylindolizidines 51 and -quinolizidines 52 were obtained irrespective of the Lewis acid used. The structures of 30 and 52 were elucidated by X-ray analysis.Item Open Access Coupled director and layer reorientation in layer tilted ferroelectric smectic liquid crystal cells(1993) Gießelmann, Frank; Zugenmaier, PeterA reversible reorientation of smectic layers in surface stabilized ferroelectric liquid crystal (SSFLC) cells with layer tilted (chevron) geometries was found by electrooptical investigations. The reorientation of the layers superimposes the reorientation of the director along the S*C tilt cone and is suppressed, if the layers are irreversibly fixed in a bookself geometry by high electric fields. Based on a potential density expansion, a dynamical model of a coupled director and layer reorientation is proposed, which leads to excellent agreement with the electrooptical behaviour of the system investigated. The fit of the model to experimental data supplies a simultaneous determination of several material and cell constants. Basic electrooptical parameters, as contrast, switching times and optical overshoot, are reproduced correctly.Item Open Access Enantioselektive Veresterung racemischer Cyanhydrine und enantioselektive Hydrolyse oder Umesterung racemischer Cyanhydrinester mittels Lipasen (Enzym-katalysierte Reaktionen ; 7)(1991) Effenberger, Franz; Gutterer, Beate; Ziegler, Thomas; Eckhardt, Elisabeth; Aichholz, ReinerIn der vorliegenden Arbeit berichten wir zusammenfassend über die enantioselektive Hydrolyse oder enantioselektive Umesterung racemischer Cyanhydrinester und über die enantioselektive Veresterung racemischer Cyanhydrine mittels Lipasen.Item Open Access Ferroelectric liquid-crystalline side group polymers - spacer length variation and comparison with the monomers(1993) Kühnpast, Kurt; Springer, Jürgen; Scherowsky, Günter; Gießelmann, Frank; Zugenmaier, PeterThe phase behaviour and the ferroelectric properties of liquid-crystalline side group polyacrylates containing an (R)-4''(1-methylheptyloxy)-4'-biphenylyloxycarbonyl-4-phenoxy moiety are compared with the properties of their monomers. A S*C phase polymorphism including monolayer and bilayer structures was found for the polymers. Some of the S*C subphases, consisting of smectic mono- or bi-layers, do not exhibit ferroelectric properties. These unusual properties do not exist for the corresponding monomeric acrylates. Therefore, one has to take into account that the polymer chain exerts a strong influence on the phase behaviour and the ferroelectric properties.Item Open Access Properties of amphiphilic terminally substituted conjugated nonaene- and 2-docosylnonaene carboxylic acids in monolayers at the air-water interface(1991) Effenberger, Franz; Meller, Paul; Ringsdorf, Helmut; Schlosser, HubertIn the present communication, we report thesynthesis of conjugated nonaene- and 2-docosylnonaene carboxylic acids with different terminal substituents. These substituents have been chosen so that their spectroscopic properties differ from those of the polyene chain; they also have specific electron donor, electron acceptor or redox properties to allow for specific and selective excitation (energy intake). Because of the amphiphilic character of these compounds, pressure-area isotherms were determined in monolayers at the air-water interface.Item Open Access Darstellung und stereoselektive Reaktionen von (R)-α-Sulfonyloxynitrilen(1991) Effenberger, Franz; Stelzer, UweHier berichten wir über eine wichtige Erweiterung des Synthesepotentials optisch aktiver Cyanhydrine durch Uberfiührung der Hydroxygruppe in eine gute Austrittsgruppe. Besonderes Interesse kommt dabei den Reaktionen der Cyanhydrinderivate zu, bei denen der Stickstoff der Cyangruppe im Molekül erhalten bleibt, da Verbindungen dieses Typs nicht direkt iüber α-Amino- oder α-Hydroxycarbonsäuren zugänglich sind.