Collect. Czech. Chem. Commun. 1990, 55, 695-703

On the origin of base concentration effect on stereo- and regioselectivity in alkoxide-promoted E2 reactions: A consequence of substrate solvation by metal ions

Jiří Závada, Magdalena Pánková and Antonín Vítek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6

Individual author index pages

Other CCCC articles of these authors

  • Petr Holý*, Martin Havlík, Miloš Tichý, Jiří Závada* and Ivana Císařová
    Synthesis and Self-Assembly of 9,9'-Spirobifluorene-2,2',7,7'-tetracarboxylic Acid and Its Tetraamide. Non-Catenated Formation of Achiral Grid Layers with Large Chiral Pores
    2006, Vol. 71, Issue 2, pp. 139–154 [Abstract]
  • Martin Bělohradský, Luděk Ridvan and Jiří Závada*
    Synthesis of Homochiral Acyclic Mono- and Bis(α-amino acid)s with Oligo(oxyethylene) Chains
    2003, Vol. 68, Issue 7, pp. 1319–1325 [Abstract]
  • Petr Sehnal, Petr Holý*, Miloš Tichý, Jiří Závada* and Ivana Císařová
    4,4'-Bipyridine-2,2',6,6'-tetracarboxamide. Synthesis and Self-Assembling Properties of the Free Base and the 1 : 1 Silver(I) Triflate Complex
    2002, Vol. 67, Issue 8, pp. 1236–1246 [Abstract]
  • Petr Holý, Jaroslav Podlaha, Ivana Císařová and Jiří Závada*
    Self-Assembly of 1,1'-Biphenyl-2,2',6,6'-tetracarboxamides. Effect of Substitution at the Amidic Nitrogen
    2001, Vol. 66, Issue 6, pp. 947–958 [Abstract]
  • Petr Holý, Jiří Závada*, Josef Zezula, Ivana Císařová and Jaroslav Podlaha
    Formation of Infinite Grids with Chiral Square Compartments by Self-Assembly of Achiral 1,1'-Biphenyl-2,2',6,6'-tetracarboxylic Acids. Effect of 4,4'-Substitution on the Grid Stacking
    2001, Vol. 66, Issue 5, pp. 820–832 [Abstract]
  • Jaroslav Podlaha, Ivana Císařová, Daniel Alexander, Petr Holý, Tomáš Kraus and Jiří Závada*
    Topological Correspondence Between Crystal Structure of 2,4,6-Trimethylbenzene-1,3,5-tris(methanaminium) 2,4,6-Trimethylbenzene-1,3,5-triacetate and Cesium Chloride
    2000, Vol. 65, Issue 10, pp. 1587–1596 [Abstract]
  • Daniel Alexander, Stanislav Böhm, Ivana Císařová, Petr Holý, Jaroslav Podlaha, Miroslav Šlouf and Jiří Závada*
    Sterically Crowded Hexaalkyl Benzene-1,2,3,4,5,6-hexakis[α-(alkoxycarbonyl)propanoates]. Synthesis and Conformation Analysis
    2000, Vol. 65, Issue 5, pp. 673–694 [Abstract]
  • Martin Chadim, Miloš Buděšínský, Jana Hodačová and Jiří Závada*
    A Covalently Bound Template in the Regioselective Synthesis of Bis(tetraazacrown)s
    2000, Vol. 65, Issue 1, pp. 99–105 [Abstract]
  • Jana Hodačová*, Jiří Závada and Peter C. Junk
    Regioselective Double Cyclisation of 1,2,4,5-Tetrakis(bromomethyl)benzene with Tosylated Diethylenetriamine. Towards Conformationally Biased Bis(perazacrown) Receptors
    1999, Vol. 64, Issue 11, pp. 1827–1832 [Abstract]
  • Tomáš Kraus, Miloš Buděšínský and Jiří Závada
    Novel Amphiphilic Cyclodextrins: Per[6-deoxy-6-(4,5-dicarboxy-1,2,3-triazol-1-yl)-2,3-di-O-methyl] Derivatives
    1998, Vol. 63, Issue 4, pp. 534–540 [Abstract]
  • Miloš Tichý, Luděk Ridvan, Miloš Buděšínský, Jiří Závada, Jaroslav Podlaha and Ivana Císařová
    Axially Chiral Bis(α-amino Acid)s and Their Deamino Analogues. Synthesis and Configurational Assignment
    1998, Vol. 63, Issue 2, pp. 211–221 [Abstract]
  • Miloš Tichý, Jana Günterová and Jiří Závada
    Novel Intramolecular Induction of Axial Chirality by a Centrally Chiral Element in the Biphenyl Series
    1997, Vol. 62, Issue 7, pp. 1080–1088 [Abstract]
  • Miloš Tichý, Luděk Ridvan and Jiří Závada
    Comparison of (R)-(-)-6,6'-Bis(3,5-dinitrobenzamido)biphenyl-2,2'-dicarboxylic and (S)-(+)-6,6'-Bis-(3,5-dinitrobenzamidomethyl)biphenyl-2,2'-dicarboxylic Acids as Chiral HPLC Selectors
    1997, Vol. 62, Issue 1, pp. 62–68 [Abstract]
  • Daniel Alexander, Petr Holý, Pavel Fiedler, Zdeněk Havlas and Jiří Závada
    Symmetrical Tris(4,6-diamino-5-methylene-2-pyrimidones): New Building Blocks for Self-Assembly of Hollow Spherical Supramolecules Locked by Hydrogen Bonds
    1996, Vol. 61, Issue 10, pp. 1464–1472 [Abstract]
  • Jaroslav Podlaha, Ivana Císařová, Martin Bělohradský and Jiří Závada
    Crystal and Molecular Structure of cis-2,2',3',2"-Tetraacetoxy-1,1':4',1"-ternaphthyl
    1996, Vol. 61, Issue 5, pp. 726–732 [Abstract]
  • Miloš Tichý and Jiří Závada
    Preparation of (R)-(-)-6,6'-Bis(3,5-dinitrobenzamido)biphenyl-2,2'-dicarboxylic Acid, a Potential Chiral HPLC Selector
    1995, Vol. 60, Issue 12, pp. 2161–2164 [Abstract]
  • Miloš Tichý, Jana Holanová, Ivo Starý, Irena G. Stará and Jiří Závada
    Axially Chiral Selectors of C2 Symmetry Bound to Silica: Synthesis and HPLC-Evaluation
    1995, Vol. 60, Issue 4, pp. 645–658 [Abstract]
  • Vladimír Král, Magdalena Pánková, Jana Günterová, Martin Bělohradský and Pavel Anzenbacher, Jr.
    Synthesis of Porphyrin Heterobinuclear Ligands
    1994, Vol. 59, Issue 3, pp. 639–648 [Abstract]
  • Martin Bělohradský, Petr Holý, Juraj Koudelka and Jiří Závada
    1,2-Bis(azacrown)ethanes: Effect of Bridge Substitution and Ring Size on Formation of Sandwich Complexes with Sodium and Potassium Ions
    1993, Vol. 58, Issue 1, pp. 153–158 [Abstract]
  • Petr Holý, Juraj Koudelka, Martin Bělohradský, Ivan Stibor and Jiří Závada
    Bis(monoazacrown ether)s: Effects of bridge length and ring size on stability and selectivity in alkali ion sandwich complex formation
    1991, Vol. 56, Issue 7, pp. 1482–1488 [Abstract]
  • Zdeněk Arnold, Miloš Buděšínský and Magdalena Pánková
    Reactivity of triformylmethane. I. Reactions of triformylmethane with selected types of amino compounds
    1991, Vol. 56, Issue 5, pp. 1019–1031 [Abstract]
  • Jiří Závada, Václav Pechanec and Oldřich Kocián
    Anion effect on alkali ion-crown complex formation in a moderately concentrated solutions: A sensitive probe of hidden interionic interactions operating in dissociating protic solvents
    1990, Vol. 55, Issue 5, pp. 1149–1161 [Abstract]
  • Jiří Závada and Magdalena Pánková
    Preferential cis-olefin formation: A striking resemblance between alkali-alkoxide and alumina promoted eliminations in low polar solvents
    1990, Vol. 55, Issue 3, pp. 704–709 [Abstract]
  • Jiří Závada, Juraj Koudelka, Petr Holý, Martin Bělohradský and Ivan Stibor
    Bis(monoazacrown ethers) with an electron-donating substituent at the hinge: A pronounced participation of hydroxyl group in formation of sodium ion sandwich complexes
    1989, Vol. 54, Issue 4, pp. 1043–1054 [Abstract]
  • Petr Holý, Martin Bělohradský, Ivan Stibor, Juraj Koudelka, David Šaman, Jana Hodačová, Antonín Holý and Jiří Závada
    Crown and azacrown ethers with pendant adenine group
    1987, Vol. 52, Issue 12, pp. 2971–2982 [Abstract]
  • Martin Bělohradský, Petr Holý, Ivan Stibor and Jiří Závada
    A versatile synthesis of oligocrown compounds with hydroxyl groups at the hinge
    1987, Vol. 52, Issue 12, pp. 2961–2970 [Abstract]
  • Martin Bělohradský, Ivan Stibor, Petr Holý and Jiří Závada
    A convenient synthesis of crown and azacrown ethers with pendant oxirane group
    1987, Vol. 52, Issue 10, pp. 2500–2507 [Abstract]
  • Ivan Stibor, Oldřich Kocián, Petr Holý and Jiří Závada
    Procedure for large-scale preparations of oligoethylene glycol toluenesulphonates
    1987, Vol. 52, Issue 8, pp. 2057–2060 [Abstract]
  • Jiří Závada, Václav Pechanec, Jaroslav Zajíček, Ivan Stibor and Antonín Vítek
    Effects of salt concentration and counterion on stability of alkali ion-18-crown-6 complexes in aqueous and methanolic solution: A conflicting evidence from potentiometric and sodium-23 NMR studies
    1985, Vol. 50, Issue 5, pp. 1184–1193 [Abstract]
  • Zdeněk Jermář, Antonín Vítek, Josef Krupička and Lubomír Šerák
    A simple method of digitalization of polarographic curves. Description of the apparatus
    1985, Vol. 50, Issue 5, pp. 1114–1120 [Abstract]
  • Jiří Závada, Josef Krupička, Oldřich Kocián and Magdalena Pánková
    Electrochemical dehalogenation of open-chain vicinal dihalides at mercury cathodes: The effect of leaving group identity on E1/2 values and on steric course
    1983, Vol. 48, Issue 12, pp. 3552–3558 [Abstract]
  • Magdalena Pánková, Oldřich Kocián, Josef Krupička and Jiří Závada
    syn-anti Dichotomy in zinc-promoted dehalogenation of open-chain vicinal dihalides: The effect of the leaving groups
    1983, Vol. 48, Issue 10, pp. 2944–2951 [Abstract]
  • Jiří Závada, Václav Pechanec and Oldřich Kocián
    The effect of counterion on alkali ion-crown complex formation: A near-paradox in dissociating solvents
    1983, Vol. 48, Issue 9, pp. 2509–2517 [Abstract]
  • Václav Pechanec, Oldřich Kocián and Jiří Závada
    Crowns in alkali alkoxide-conjugate acid solutions: A remarkably low propensity to complex formation
    1983, Vol. 48, Issue 4, pp. 1144–1157 [Abstract]
  • Václav Pechanec, Oldřich Kocián and Jiří Závada
    Effects of structure and concentration on ionic association in alkali alkoxide-conjugate acid solutions: Reluctance to formation of ion-pair aggregates
    1982, Vol. 47, Issue 12, pp. 3405–3411 [Abstract]
  • Antonín Vítek and Josef Krupička
    Distinguishing some types of one-electron reversible processes according to different polarographic wave forms
    1982, Vol. 47, Issue 11, pp. 2838–2848 [Abstract]
  • Helena Velgová, Jorga Smolíková, Antonín Trka and Antonín Vítek
    Cyclopropyl→cyclobutyl rearrangement in intramolecular cyclization of 3,5-bridged B-secoandrostane-6,7(or 5,7)-diols and mass spectra of products
    1982, Vol. 47, Issue 8, pp. 2280–2290 [Abstract]
  • Oldřich Kocián, Karel Stránský and Jiří Závada
    Heteroanalogues of 1-triacontanol
    1982, Vol. 47, Issue 5, pp. 1356–1366 [Abstract]
  • Oldřich Kocián, Karel Stránský and Jiří Závada
    Unsaturated analogues of 1-triacontanol
    1982, Vol. 47, Issue 5, pp. 1346–1355 [Abstract]
  • Jiří Závada, Magdalena Pánková and Antonín Vítek
    The search for the active base operating in alkoxide promoted E2 reactions in low polar solvents: A kinetic analysis of the elusive problem
    1981, Vol. 46, Issue 13, pp. 3247–3263 [Abstract]
  • Václav Pechanec, Oldřich Kocián, Vlastimil Halaška, Magdalena Pánková and Jiří Závada
    Degrees of association of alkali tert-butoxides in tert-butanol in the absence and in the presence of crowns: An ebulliometric study
    1981, Vol. 46, Issue 9, pp. 2166–2177 [Abstract]
  • Jiří Závada, Magdalena Pánková, Richard A. Bartsch and Bong Rae Cho
    The effect of base concentration on orientation in E2 reactions: A common feature in metal alkoxide promoted olefin formation from alkyl halides and tosylates
    1981, Vol. 46, Issue 4, pp. 850–855 [Abstract]
  • Zuzana Machková and Jiří Závada
    The effect of phenyl substituents on elimination stereochemistry: A mechanistic manifold in alkoxide promoted decomposition of 1-phenyl-1-propyltrimethylammonium ion
    1981, Vol. 46, Issue 4, pp. 833–849 [Abstract]
  • Magdalena Pánková and Jiří Závada
    The effect of crown ether on steric hindrance to base approach in bimolecular elimination: evidence against clump aggregate model of ion-paired alkoxide base
    1980, Vol. 45, Issue 11, pp. 3150–3159 [Abstract]
  • Jiří Závada and Magdalena Pánková
    The effect of steric size of leaving group on rates of the competing syn- and anti-pathways in biomolecular elimination
    1980, Vol. 45, Issue 8, pp. 2171–2178 [Abstract]
  • Roman Řeřicha, Antonín Vítek, Dana Kolihová, Václav Sychra, Zdeněk Šír and Jiří Hetflejš
    Asymmetric distribution of a metal in a heterogenized homogeneous catalyst
    1979, Vol. 44, Issue 11, pp. 3183–3193 [Abstract]
  • Jiří Závada and Magdalena Pánková
    The syn-anti dichotomy in bimolecular elimination of alkyltrimethylammonium salts: Steric and polar effects on rates and orientation in the competing pathways
    1979, Vol. 44, Issue 4, pp. 1273–1295 [Abstract]
  • Jiří Závada and Magdalena Pánková
    E2-SN2 Competition: The effect of crown ether, leaving group and solvent in the reaction of 1-nonyl derivatives with potassium tert-butoxide
    1978, Vol. 43, Issue 4, pp. 1080–1086 [Abstract]