Collect. Czech. Chem. Commun. 1968, 33, 4027-4038
https://doi.org/10.1135/cccc19684027

Stereochemical studies. LIII. Steric course of cycloalkyl 'onium base eliminations: Direct evidence for the syn-anti elimination dichotomy using deuterium labelled cyclodecyl derivatives

J. Závada, M. Svoboda and J. Sicher

Individual author index pages


Other CCCC articles of these authors

  • M. Svoboda, A. T. Yudin and J. Sicher
    Stereochemical studies. XL. Synthesis of 4,4,8,8-tetramethylcyclodecanecarboxylic acid and 1,1,5,5-tetramethylcyclodecane: compounds possessing a "deformed" cyclodecane conformation
    1967, Vol. 32, Issue 4, pp. 1625–1630 [Abstract]
  • M. Pánková and J. Závada
    Alkyl structure-reactivity relationships in anti-elimination of open-chain tosylates: On steric hindrance to approach of associated and dissociated tert-butoxide base
    1977, Vol. 42, Issue 12, pp. 3439–3448 [Abstract]
  • J. Závada and M. Pánková
    Alkyl structure-selectivity relationships E2 reactions of open-chain tosylates: Steric effects in the anti-pathway induced by dissociated and associated tert-butoxide base
    1977, Vol. 42, Issue 12, pp. 3421–3438 [Abstract]
  • M. Pánková and J. Závada
    The effect of hydrogen bonding on orientation in anti-E2 reactions
    1977, Vol. 42, Issue 7, pp. 2161–2166 [Abstract]
  • M. Pánková and J. Závada
    Geometrical and positional orientation in anti-E2 reactions: The effect of base association in a wider scale of transition states
    1977, Vol. 42, Issue 6, pp. 1981–1991 [Abstract]
  • Z. Arnold and M. Svoboda
    Preparation of dinitriles of aminomalonic acids
    1977, Vol. 42, Issue 4, pp. 1175–1178 [Abstract]
  • M. Svoboda, V. Král and Z. Arnold
    Preparation of N,N-disubstituted aminomalonaldehydes
    1977, Vol. 42, Issue 3, pp. 1027–1034 [Abstract]
  • J. Závada, M. Pánková and M. Svoboda
    syn-anti Duality in E2 reactions: The effects of leaving group and base association in the competing pathways
    1976, Vol. 41, Issue 12, pp. 3778–3798 [Abstract]
  • J. Závada, M. Pánková and Z. Arnold
    Silver perchlorate promoted reactions: Arylmethylation of aromatics by bromomethylarenes
    1976, Vol. 41, Issue 6, pp. 1777–1790 [Abstract]
  • J. Smolíková, M. Havel, S. Vašíčková, A. Vítek, M. Svoboda and K. Bláha
    Conformation of 1-aza-2-cycloalkanones with large rings: Infrared spectroscopic study
    1974, Vol. 39, Issue 2, pp. 459–467 [Abstract]
  • J. Smolíková, M. Havel, S. Vašíčková, A. Vítek, M. Svoboda and K. Bláha
    Conformation of medium ring lactams: Infrared spectroscopic study
    1974, Vol. 39, Issue 1, pp. 293–306 [Abstract]
  • M. Pánková, J. Krupička and J. Závada
    Rates of the Menschutkin reaction in alkyldimethylamines: The effect of alkyl structure and solvent
    1974, Vol. 39, Issue 1, pp. 167–170 [Abstract]
  • J. Závada, M. Pánková and M. Svoboda
    Stereochemical studies. LXXIV. The alkyl structure-reactivity relationship in Cope elimination of alkyldimethylamine oxides
    1973, Vol. 38, Issue 7, pp. 2102–2120 [Abstract]
  • Z. Arnold, J. Kahovcová, M. Pánková, M. Svoboda, M. Tichý and F. Šorm
    Natural and synthetic materials with the insect hormone activity. XIV. Synthesis of substituted phenyl geranyl ethers and related compounds
    1973, Vol. 38, Issue 1, pp. 261–269 [Abstract]
  • M. Svoboda and J. Závada
    Stereochemical studies. LXX. The role of base ion-pairing in bimolecular elimination: The effect of a base counterion on the steric course
    1972, Vol. 37, Issue 12, pp. 3902–3904 [Abstract]
  • R. Řeřicha, A. Vítek, S. Vašíčková, M. Pánková and J. Závada
    The infrared spectra of 1-decenes deuterated on the double bond. A comparison with the vinyl halides-dx
    1972, Vol. 37, Issue 11, pp. 3749–3761 [Abstract]
  • M. Pánková, A. Vítek, S. Vašíčková, R. Řeřicha and J. Závada
    Stereochemical studies. LXIX. Contribution of syn- and anti-elimination to the monosubstituted olefin formation from 1-decyltrimethylammonium base
    1972, Vol. 37, Issue 10, pp. 3456–3466 [Abstract]
  • M. Tichý and J. Sicher
    Stereochemical studies. LXV. Synthetic studies in the tricyclo[4,4,0,03,8]decane and tricyclo[4,3,1,03,7]decane series: The synthesis of twistene
    1972, Vol. 37, Issue 9, pp. 3106–3116 [Abstract]
  • J. Závada, M. Pánková and J. Sicher
    Stereochemical studies. LXIII. The contribution of syn- and anti-elimination to olefin formation in branched open-chain systems: The effect of alkyl structure on steric course of bimolecular elimination
    1972, Vol. 37, Issue 7, pp. 2414–2435 [Abstract]
  • J. Sicher, M. Svoboda, M. Pánková and J. Závada
    Stereochemical studies. LXII. The Hofmann-Saytzeff and the syn-anti elimination dichotomy: A relationship between the two phenomena
    1971, Vol. 36, Issue 11, pp. 3633–3649 [Abstract]
  • J. Sicher, J. Závada and M. Pánková
    Stereochemical studies. LXI. The contribution of syn- and anti-elimination to olefin formation in open-chain systems: 5-Decyl and 5-nonyl trimethylammonium bases and tosylates
    1971, Vol. 36, Issue 9, pp. 3140–3164 [Abstract]
  • J. Sicher, M. Pánková, J. Závada, L. Kniežo and A. Orahovats
    Stereochemical studies. LX. Steric course of bimolecular elimination in bicyclo[2.2.2]octyl onium bases and tosylates
    1971, Vol. 36, Issue 9, pp. 3128–3139 [Abstract]
  • M. Tichý, S. Vašíčková, A. Vítek and J. Sicher
    Stereochemical studies. LIX. Flattened chair and twist-boat conformations in cis-2-dimethylaminocyclohexanols
    1971, Vol. 36, Issue 4, pp. 1436–1447 [Abstract]
  • M. Tichý and J. Sicher
    Stereochemical studies. LVIII. Synthesis of trans-anti-trans-perhydro-as-indacene, a system containing a frozen cyclohexane chair
    1971, Vol. 36, Issue 4, pp. 1426–1435 [Abstract]
  • M. Tichý, S. Vašíčková, S. V. Arakelian and J. Sicher
    Stereochemical studies. LVII. Conformational equilibria in trans-2-amino- and trans-2-dimethylaminocyclohexanols: Evaluation of the gauche interactions between OH and NR2
    1970, Vol. 35, Issue 5, pp. 1522–1535 [Abstract]
  • A. Orahovats, M. Tichý and J. Sicher
    Stereochemical studies. LVI. Evaluation of vicinal eclipsing interactions between some groups on a bicyclo[2,2,2]octane system
    1970, Vol. 35, Issue 3, pp. 838–843 [Abstract]
  • M. Tichý, A. Orahovats and J. Sicher
    Stereochemical studies. LV. Evaluation of some 1,3-syn-axial interactions in six-membered ring systems
    1970, Vol. 35, Issue 2, pp. 459–468 [Abstract]
  • M. Havel, M. Svoboda and J. Sicher
    Stereochemical studies. LIV. trans-1,2-Dibromocyclodecane: The synthesis of an elusive compound
    1969, Vol. 34, Issue 1, pp. 340–343 [Abstract]
  • J. Sicher, M. Tichý, J. Závada and J. Krupička
    Stereochemical studies. LII. Rates of the Menschutkin reaction in cyclohexyldimethylamines. Some unusual rate effects in a simple reaction
    1968, Vol. 33, Issue 5, pp. 1438–1450 [Abstract]
  • M. Havel, J. Krupička, M. Svoboda, J. Závada and J. Sicher
    Stereochemical studies. LI. Effect of ring size on the rates of quaternization of the N-methylazacycloalkanes
    1968, Vol. 33, Issue 5, pp. 1429–1437 [Abstract]
  • M. Svoboda, J. Závada and J. Sicher
    Stereochemical studies. L. The mechanism of bimolecular elimination of cycloalkyl tosylates. The scope of syn-elimination: Dependence on reaction conditions and substrate structure
    1968, Vol. 33, Issue 5, pp. 1415–1428 [Abstract]
  • J. Závada, J. Krupička and J. Sicher
    Stereochemical studies. IL. The mechanism of cycloalkene formation from cycloalkyl bromides. The scope of the syn-anti bimolecular elimination dichotomy
    1968, Vol. 33, Issue 5, pp. 1393–1414 [Abstract]
  • J. Sicher and J. Závada
    Stereochemical studies. XLVIII. Effect of base and solvent on the steric course and mechanism of cycloalkene formation in 'onium salt eliminations
    1968, Vol. 33, Issue 4, pp. 1278–1293 [Abstract]
  • M. Tichý and J. Sicher
    Stereochemical studies. XLV. Epimerisation equilibria in conformationally biased 2-methylcyclohexanecarboxylates and cyanides
    1968, Vol. 33, Issue 1, pp. 68–75 [Abstract]
  • J. Závada and J. Sicher
    Stereochemical studies. XLIV. The syn-anti elimination dichotomy - A general feature in cycloalkene formation from 'onium salts in protic solvents
    1967, Vol. 32, Issue 10, pp. 3701–3712 [Abstract]
  • J. Sicher and M. Tichý
    Stereochemical studies. XLIII. Epimerisation equilibria in conformationally biased and fixed 2-methylcyclohexanols: Evaluation of CH3-OH gauche interactions
    1967, Vol. 32, Issue 10, pp. 3687–3700 [Abstract]
  • J. Krupička and J. Závada
    Polarography of cycloalkyldimethylamine oxides. A polarographic method for the kinetic study of the amine oxide elimination reaction (Cope elimination)
    1967, Vol. 32, Issue 8, pp. 2797–2808 [Abstract]
  • J. Sicher and J. Závada
    Stereochemical studies. XLII. The effect of ring size on the rate of formation of cis- and trans-cycloalkenes from cycloalkyltrimethylammonium salts: Evidence on the simultaneous operation of syn- and anti-mechanisms in bimolecular elimination
    1967, Vol. 32, Issue 6, pp. 2122–2133 [Abstract]
  • M. Svoboda, J. Závada and J. Sicher
    Stereochemical studies. XLI. Solvolysis of cyclodecyl tosylates: Steric course of the reaction and conformational analysis
    1967, Vol. 32, Issue 6, pp. 2104–2121 [Abstract]
  • J. Závada, J. Krupička and J. Sicher
    Stereochemical studies. XXXIX. The effect of ring size on the rate of formation of cis- and trans-cycloalkanes from cycloalkyldimethylamine oxides
    1966, Vol. 31, Issue 11, pp. 4273–4285 [Abstract]
  • M. Tichý, F. Šipoš and J. Sicher
    Stereochemical studies. XXXVIII. Conformational energies for the axial-equatorial change in different cyclohexyl systems
    1966, Vol. 31, Issue 7, pp. 2889–2898 [Abstract]
  • J. Sicher, M. Tichý and F. Šipoš
    Stereochemical studies. XXXVII. Dissociation constants of some 2-methylcyclohexanecarboxylic acids. Conformational equilibria and the preferred rotational conformations of the carboxyl group on the cyclohexane ring
    1966, Vol. 31, Issue 5, pp. 2238–2256 [Abstract]
  • J. Krupička, J. Závada and J. Sicher
    Stereochemical studies. XXXV. The polarographic reduction of cycloalkyl bromides: E1/2 values and mechanism
    1965, Vol. 30, Issue 10, pp. 3570–3575 [Abstract]
  • M. Svoboda and J. Sicher
    Stereochemical studies. XXXIV. The reactivity of large ring compounds. The course of intramolecular displacement reactions in cyclic systems
    1965, Vol. 30, Issue 9, pp. 2948–2959 [Abstract]
  • J. Závada and J. Sicher
    Stereochemical studies. XXXII. The preferred formation of cis-olefin in bimolecular 'onium salt eliminations
    1965, Vol. 30, Issue 2, pp. 438–444 [Abstract]
  • J. Sicher, M. Svoboda and J. Závada
    Stereochemical studies. XXXI. The metal-liquid ammonia reduction of alkyl-substituted cyclodecynes and cyclodeca-1,2-dienes: The mechanism of cycloalkyne reduction
    1965, Vol. 30, Issue 2, pp. 421–437 [Abstract]
  • M. Svoboda, J. Závada and J. Sicher
    Stereochemical studies. XXX. The anomalous course of metal-ammonia reduction of some cycloalkynes
    1965, Vol. 30, Issue 2, pp. 413–420 [Abstract]
  • M. Pánková and J. Sicher
    Stereochemical studies. XXIX. Steric effects in an intramolecular displacement reaction in open-chain systems
    1965, Vol. 30, Issue 2, pp. 388–412 [Abstract]
  • J. Sicher, M. Tichý, F. Šipoš, M. Svoboda and Jiří Jonáš
    Stereochemical studies. XXVIII. Evaluation of the contribution of hydroxyl to the dissociation constants of 2-hydroxycarboxylic acids and 2-aminoalcohols as a function of conformation
    1964, Vol. 29, Issue 7, pp. 1561–1576 [Abstract]
  • J. Závada, J. Krupička and J. Sicher
    Stereochemical studies. XXVI. Determination of the stereochemistry of vicinal dibromides by polarographic reduction
    1963, Vol. 28, Issue 7, pp. 1664–1674 [Abstract]
  • J. Sicher, M. Cherest, Y. Gault and H. Felkin
    Stereochemical studies. XXV. Diastereoisomeric β-hydroxyphenyl and β-hydroxyolefin derivatives: Assignment of configuration by spectroscopic intramolecular hydrogen bond determination
    1963, Vol. 28, Issue 1, pp. 72–81 [Abstract]
  • M. Tichý, J. Šipoš and J. Sicher
    Stereochemical studies. XXIV. A study of ring deformations in 2-aminocyclohexanol derivatives by spectroscopic intramolecular hydrogen bond determination
    1962, Vol. 27, Issue 12, pp. 2907–2924 [Abstract]
  • F. Šipoš, J. Krupička, M. Tichý and J. Sicher
    Stereochemical studies. XXIII. The 4-t-butyl-2-methylcyclohexanols - Synthesis and rates of chromic acid oxidation
    1962, Vol. 27, Issue 9, pp. 2079–2089 [Abstract]
  • J. Sicher, J. Závada and M. Svoboda
    Stereochemical studies. XXII. Bromine addition to medium ring cycloölefins: A transannular reaction
    1962, Vol. 27, Issue 8, pp. 1927–1938 [Abstract]
  • V. Horák and J. Závada
    Schwefelanaloga von Tropan-Derivaten II. Derivate der epimeren 8-Thia-bicyclo(1,2,3)octan-3-ole
    1962, Vol. 27, Issue 5, pp. 1224–1228 [Abstract]
  • J. Sicher, M. Tichý, F. Šipoš and M. Pánková
    Stereochemical studies. XX. Conformational studies on the 2-amino-4-t-butylcyclohexanols; An approach to quantitative conformational analysis of neighbouring group participation and solvolysis in 1,2-difunctional cyclohexane derivatives
    1961, Vol. 26, Issue 9, pp. 2418–2434 [Abstract]
  • F. Mareš, J. Roček and J. Sicher
    The chromic acid oxidation of cycloparaffins: Correlation between reactivity and thermochemical strain, and notes on the reaction mechanism
    1961, Vol. 26, Issue 9, pp. 2355–2369 [Abstract]
  • J. Sicher, F. Šipoš and M. Tichý
    Stereochemical studies. XIX. Conformational studies on the 2-amino-4-t-butylcyclohexanols; Synthesis of the four stereoisomers
    1961, Vol. 26, Issue 3, pp. 847–866 [Abstract]
  • J. Sicher, F. Šipoš and Jiří Jonáš
    Stereochemical studies. XVIII. Synthesis and dissociation constants of cis- and trans-cycloheptane- and cycloöctane-1,2-dicarboxylic acids
    1961, Vol. 26, Issue 1, pp. 262–275 [Abstract]
  • J. Sicher, M. Rajšner, J. Rudinger, M. Eckstein and F. Šorm
    Amino-acids and peptides. XXVIII. Synthesis of threo- and erythro-DL-α,γ-diamino-β-hydroxybutyric acid (γ-aminothreonine and γ-aminoallothreonine)
    1959, Vol. 24, Issue 11, pp. 3719–3729 [Abstract]
  • M. Tichý, Jiří Jonáš and J. Sicher
    Stereochemical studies. XVII. Dissociation constants of cyclohexanecarboxylic acids and cyclohexylamines and conformational equilibria
    1959, Vol. 24, Issue 10, pp. 3434–3441 [Abstract]
  • J. Sicher, M. Pánková, Jiří Jonáš and M. Svoboda
    Stereochemical studies. XVI. Stereospecific processes in open-chain 3-aminoalcohols. Synthesis of erythro- and threo-4-aminopentan-2-ol
    1959, Vol. 24, Issue 8, pp. 2727–2740 [Abstract]
  • J. Sicher, M. Horák and M. Svoboda
    Stereochemical studies. XV. The effect of ring size and configuration on the infrared spectra of the 2-aminocyclanols
    1959, Vol. 24, Issue 3, pp. 950–957 [Abstract]
  • J. Sicher, Jiří Jonáš, M. Svoboda and O. Knessl
    Stereochemical studies. XIV. The effect of ring size and configuration on the rate of intramolecular cyclisation of the N-thiobenzoylderivatives of cis- and trans-2-aminocyclanols
    1958, Vol. 23, Issue 12, pp. 2141–2154 [Abstract]
  • J. Sicher and M. Svoboda
    Stereochemical studies. XIII. The effect of ring size and configuration on the rate of intramolecular cyclisation of cis- and trans-2-benzamidocycloalkyl methanesulphonates
    1958, Vol. 23, Issue 11, pp. 2094–2110 [Abstract]
  • J. Sicher and M. Tichý
    Stereochemical studies. XII. The absolute configuration of conhydrine and ψ-conhydrine
    1958, Vol. 23, Issue 11, pp. 2081–2093 [Abstract]
  • M. Svoboda, M. Tichý and J. Sicher
    Stereochemical studies. XI. Synthesis of cis- and trans-2-aminocyclotetradecanol and 2-aminocyclopentadecanol
    1958, Vol. 23, Issue 10, pp. 1958–1964 [Abstract]
  • M. Svoboda, Jiří Jonáš and J. Sicher
    Stereochemical studies. X. The effect of ring size and configuration on the basicity of the 2-aminocyclanols
    1958, Vol. 23, Issue 8, pp. 1551–1558 [Abstract]
  • M. Svoboda and J. Sicher
    Stereochemical studies. IX. Hofmann degradation of quaternary bases of some medium and large ring cis- and trans-2-aminoalcohols; Configurational assignment
    1958, Vol. 23, Issue 8, pp. 1540–1550 [Abstract]
  • J. Sicher and M. Svoboda
    Stereochemical studies. VIII. Synthesis of medium and large ring cis- and trans-2-aminocyclanols
    1958, Vol. 23, Issue 7, pp. 1252–1279 [Abstract]
  • P. Zuman, J. Sicher, J. Krupička and M. Svoboda
    Stereochemical studies. VII. Periodate oxidation of diastereoisomeric diols of the type R.CH(OH).CH(OH).R'
    1958, Vol. 23, Issue 7, pp. 1237–1251 [Abstract]
  • J. Smrt, J. Beránek, J. Sicher and F. Šorm
    Synthesis of 4-amino-3-isoxazolidinone (cycloserine)
    1957, Vol. 22, Issue 1, pp. 262–273 [Abstract]
  • M. Svoboda and J. Sicher
    Stereochemical studies. VI. Configuration of the 1-phenylpropane-1,2-diols; Steric course of the hydrolysis of cis- and trans-1-phenyl-2-methylethyleneoxide
    1955, Vol. 20, Issue 6, pp. 1452–1455 [Abstract]
  • J. Sicher, M. Svoboda and J. Farkaš
    Stereochemical studies. V. The synthesis and configuration of the two racemic β-phenylcysteines
    1955, Vol. 20, Issue 6, pp. 1439–1451 [Abstract]
  • M. Svoboda, J. Sicher, J. Farkaš and M. Pánková
    Stereochemical studies. IV. Reaction of Δ2-oxazolines with thioacetic acid. Syntheses of some diacyl-1,2-aminothiols
    1955, Vol. 20, Issue 6, pp. 1426–1438 [Abstract]
  • J. Sicher and M. Pánková
    Stereochemical studies. III. Steric course of the reaction of N-acyl derivatives of 1,2-aminoalcohols with thionyl chloride
    1955, Vol. 20, Issue 6, pp. 1409–1425 [Abstract]
  • J. Sicher and M. Svoboda
    Stereochemical studies. II. Reactions of N-acyl derivatives of 1,2-aminothiols in acid solution
    1955, Vol. 20, Issue 6, pp. 1402–1408 [Abstract]
  • J. Farkaš and J. Sicher
    Stereochemical studies. I. Steric course of the acid-catalysed cyclisation of N-thiobenzoyl derivatives of 1,2-aminoalcohols. A new stereospecific reaction
    1955, Vol. 20, Issue 6, pp. 1391–1401 [Abstract]
  • J. Sicher
    Stereochemical studies; Introductory remarks
    1955, Vol. 20, Issue 6, pp. 1389–1390 [Abstract]
  • F. Šorm, J. Beránek, J. Smrt and J. Sicher
    Reaktionen des Ketens V. Über die Reaktion des Ketens mit substituierten Malonylchloriden
    1955, Vol. 20, Issue 3, pp. 593–597 [Abstract]
  • F. Šorm, V. Benešová, J. Krupička, V. Šneberk, L. Dolejš, V. Herout and J. Sicher
    On terpenes. LXV. The constitution of lactaroviolin. Synthesis of 1-ethyl-4-methyl-7-isopropylazulene and 4-ethyl-1-methyl-7-isopropylazulene
    1955, Vol. 20, Issue 1, pp. 227–240 [Abstract]
  • J. Novák, F. Šorm and J. Sicher
    On terpenes. LXIII. Total synthesis of chamazulene. A simple general synthesis of 1,4,7-trisubstituted azulenes
    1954, Vol. 19, Issue 6, pp. 1264–1273 [Abstract]
  • J. Farkaš and J. Sicher
    Studies in the chloramphenicol series. IX. Side-chain mercapto analogues and thiazolines
    1954, Vol. 19, Issue 4, pp. 754–765 [Abstract]
  • M. Svoboda, J. Farkaš and J. Sicher
    Studies in the chloramphenicol series. VIII. Some unsaturated derivatives
    1954, Vol. 19, Issue 3, pp. 545–550 [Abstract]
  • J. Sicher, M. Svoboda, J. Farkaš and F. Šorm
    Studies in the chloramphenicol series. VII. The side reactions in the reduction of dehydrochloramphenicol
    1954, Vol. 19, Issue 2, pp. 317–329 [Abstract]
  • J. Sicher, M. Svoboda, M. Hrdá, J. Rudinger and F. Šorm
    Studies in the chloramphenicol series. VI. Steric course of the reduction of dehydrochloramphenicol and related compounds
    1953, Vol. 18, Issue 4, pp. 487–499 [Abstract]
  • J. Farkaš and J. Sicher
    Studies in the chloramphenicol series. V. Side-chain chlorinated analogues, and oxazolines
    1953, Vol. 18, Issue 4, pp. 469–486 [Abstract]
  • J. Sicher, J. Farkaš and F. Šorm
    Studies in the chloramphenicol series. IV. Synthesis of 1-(p-nitrophenyl)-2-hydroxymethyl-2-dichloroacetamido-1,3-propandiol and a correction
    1953, Vol. 18, Issue 1, pp. 102–105 [Abstract]
  • F. Šorm and J. Sicher
    On the synthesis of pseudoconhydrine. I. Synthesis of one isomeride of rac. 2-propyl-5-oxypiperidine
    1949, Vol. 14, pp. 331–344 [Abstract]