PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2006 | 4 | 4 | 808-821
Tytuł artykułu

Synthesis and stereochemistry of some new 1,3,5-tris(1,3-dioxan-2-yl)-benzene derivatives

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The synthesis and the stereochemistry of new 1,3,5-tris(1,3-dioxan-2-yl)-benzene derivatives are reported. The anancomeric structure and the axial orientation of the aryl group with respect to all 1,3-dioxane rings, and the cis-trans isomerism of some of the compounds are revealed. The data are supported by NMR investigations and by the molecular structure of one compound determined by single crystal X-ray diffractometry.
Wydawca
Czasopismo
Rocznik
Tom
4
Numer
4
Strony
808-821
Opis fizyczny
Daty
wydano
2006-12-01
online
2006-12-01
Twórcy
  • Organic Chemistry Department and CCOCCAN, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania
autor
  • UMR C 6626, Université de Rennes I, 35042, Rennes, Cedex, France
  • Organic Chemistry Department and CCOCCAN, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania
autor
  • Organic Chemistry Department and CCOCCAN, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania , igrosu@chem.ubbcluj.ro
  • IRCOF, UMR 6014, Faculté des Sciences de Rouen, Université de Rouen, 76821, Mont Saint Aignan, Cedex, France
  • Faculty of Engineering, “Aurel Vlaicu” University, 310025, Arad, Romania
autor
  • IRCOF, UMR 6014, Faculté des Sciences de Rouen, Université de Rouen, 76821, Mont Saint Aignan, Cedex, France
Bibliografia
  • [1] I. Grosu, S. Mager, G. Plé, N. Plé, A. Toscano, E. Mesaros and E. Martinez: “Synthesis and Stereochemistry of Some 1,3-Dioxane Diacetals of o-Phtaldialdehyde”, Liebigs Annalen/Recueil, (1997), pp. 2371–2377
  • [2] I. Grosu, S. Mager, L. Toupet, G. Plé, E. Mesaros and A. Mihis: “Synthesis and Stereochemistry of Some New 1,3-Dioxane Derivatives of 1,4-Benzenedicarbaldehyde”, Acta Chem. Scand, Vol. 52, (1998), pp. 366–371 http://dx.doi.org/10.3891/acta.chem.scand.52-0366[Crossref]
  • [3] I. Grosu, S. Mager, E. Mesaros and G. Plé: “Synthesis and Stereochemistry of Some New 1,3-Dioxane Derivatives of o-Phthaldialdehyde”, Heterocyclic Commun., Vol. 4, (1998), pp. 53–58
  • [4] I. Grosu, L. Muntean, L. Toupet, G. Plé, M. Pop, M. Balog, S. Mager and E. Bogdan: “Synthesis and Stereochemistry of Some New 1,3-Dioxane Derivatives Obtained From 1,4-Diacetylbenzene”, Monatsh. Chem., Vol. 133, (2002), pp. 631–641 http://dx.doi.org/10.1007/s007060200035[Crossref]
  • [5] L. Muntean, M. Pop, I. Grosu, S. Mager, G. Plé, A. Nan and E. Bogdan: “Synthesis and Stereochemistry of Some New 1,3-Dioxane Derivatives of 1,3-Diacetylbenzene”, Rev. Roum. Chim., Vol. 47, (2002), pp. 121–126
  • [6] M. Balog, S. Tötös, C.M. Florian, I. Grosu, G. Plé, L. Toupet, Y. Ramondenc and N. Dinca: “Synthesis and Stereochemistry of Some New 1,3-Dioxane Derivatives Obtained From 2-Acetyl and 2,6-Diacetylpyridine”, Heterocyclic Commun., Vol. 10, (2004), pp. 139–144.
  • [7] E.L. Eliel, S.H. Wilen and M.P. Doyle: Basic Organic Stereochemistry, Wiley & Sons, New York, 2001, p. 442.
  • [8] F.W. Nader and E.L. Eliel: “Conformational analysis. XXII. Conformational equilibria in 2-substituted 1,3-dioxanes”, J. Am. Chem. Soc., Vol. 92, (1970), pp. 3050–3055 http://dx.doi.org/10.1021/ja00713a022[Crossref]
  • [9] S. Mager, I. Hopartean, M. Horn and I. Grosu: “1H-NMR Spectra and Stereochemistry of Some 2,5-Substituted-1,3-Dioxanes”, Studia Univ. “Babes-Bolyai”, Chemia, Vol. 24, (1979), pp. 32–38
  • [10] M.J.O. Anteunis, D. Tavernier and F. Borremans: “A review on the conformational aspects in the 1,3-dioxane system”, Heterocycles, Vol. 4, (1976), pp. 293–371 http://dx.doi.org/10.3987/R-1976-02-0293[Crossref]
  • [11] W.F. Bailey and E.L. Eliel: “Conformational analysis. XXIX. 2-Substituted and 2,2-disubstituted 1,3-dioxanes. Generalized and reverse anomeric effects”, J. Am. Chem. Soc., Vol. 96, (1974), pp. 1798–1806 http://dx.doi.org/10.1021/ja00813a025[Crossref]
  • [12] I. Grosu, G. Plé, S. Mager, E. Mesaros, A. Dulau and C. Geco: “Study on the atropoisomerism of some new 2-aryl-1,3-dioxanes”, Tetrahedron, Vol. 54, (1998), pp. 2905–2916 http://dx.doi.org/10.1016/S0040-4020(98)83026-3[Crossref]
  • [13] M. Balog, I. Grosu, G. Plé, Y. Ramondenc, E. Condamine and R. Varga: “Design and Synthesis of New Macrocyclic Cyclophanes Using 1,3-Dioxane Units as Bridges: A Molecular “Rocking Chair”, J. Org. Chem., Vol. 69, (2004), pp. 1337–1345 http://dx.doi.org/10.1021/jo0353987[Crossref]
  • [14] N. Bogdan, I. Grosu, G. Benoît, L. Toupet and Y. Ramondenc: “Condamine E., Silaghi-Dumitrescu I., Plé G.: “Molecular Rotors: Design, Synthesis, Structural Analysis and Silver Complex of New [7.7] Cyclophanes”, Org. Lett., Vol. 8, (2006), pp. 2619–2622 http://dx.doi.org/10.1021/ol0610845[Crossref]
  • [15] J. Blankenstein and J. Zhu: “Conformation-Directed Macrocyclization Reactions”, Eur. J. Org. Chem., (2005), pp. 1949–1964 [Crossref]
  • [16] I. Grosu, B.C. Camacho, A. Toscano, G. Plé, S. Mager, R. Martinez and R.R. Gavino: “Synthesis and Stereochemistry of Some New Brominated Spiro 1,3-Dioxanes”, J. Chem. Soc. Perkin Trans 1, Vol. 5, (1997), pp. 775–782 http://dx.doi.org/10.1039/a604734c[Crossref]
  • [17] E. Bogdan, I. Grosu, E. Mesaros, L. Toupet, G. Plé, S. Mager and L. Muntean: “Considerations on the Stereoselective Synthesis of Dibrominated Spiro-1,3-Dioxanes. Synthesis and Stereochemistry of Monobrominated Precursors”, J. Chem. Soc. Perkin Trans 1, Vol. 21, (2000), pp. 3635–3639 http://dx.doi.org/10.1039/b004282j[Crossref]
  • [18] Z. Otwinowski and W. Minor: “Processing of X-ray Diffraction Data Collected in Oscillation Mode, in Methods in Enzymology”, In: C.W. Carter and R.M. Sweet (Eds.): Macromolecular Crystallography, Part A, Vol. 276, Academic Press, London, 1997, pp. 307–326.
  • [19] Nonius, KappaCCD Software, Nonius BV, Delft, The Netherlands, 1999.
  • [20] A. Altomare, M.C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori and R. Spagna: “Sir97: a new tool for crystal structure determination and refinement”, J. Appl. Crystal., (1998), Vol. 31, pp. 74–77 http://dx.doi.org/10.1107/S002188989700945X[Crossref]
  • [21] G.M. Sheldrick: SHELX97, Program for the Refinrement of Crystal Structures, Univ. of Göttingen, Germany, 1997.
  • [22] A.J.C. Wilson (Ed.): International Tables for X-ray Crystallography, Vol. C, Kluwer Academic Publishers, Dordrecht, 1992.
  • [23] A.L. Spek: PLATON. A multipurpose crystallographic tool, Utrecht University, Utrecht, The Netherlands, 1998.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0040-2
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.