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Boron Trifluoride Mediated Addition of Nucleophiles to endo- and exo-Substituted Norbornene Derivatives

  • Alper İşleyen , Tuğmac Sayraç and Özdemir Doğan EMAIL logo
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 59 Issue 1

Abstract

Remote substituent effects on the regioselectivity and stereoselectivity in the boron trifluoride mediated addition of nucleophiles (iodide and bromide) to endo- and exo-2-substituted norbornene derivatives have been investigated. The main products of the reactions resulted from the regioselective addition of nucleophiles to the double bond of norbornene derivatives. Products resulting from the Wagner-Meerwein type rearrangement were also isolated in considerable amounts. All of the reactions gave the addition products in reasonably good yields with high regioselectivity. The endo/exo selectivity, on the other hand, changed depending on the nucleophile and the substrate.

Keywords : Remote Substituent Effects; endo/exo Selectivity; Regioselectivity; Nucleophilic Additions; π-Facial Selectivity
Received: 2003-10-1
Published Online: 2014-6-2
Published in Print: 2004-1-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. The Low-Temperature Polymorph of Tetramethyldiphosphinebis( monoborane): Insight into the Stabilization of Different Rotational Isomers in the Solid State
  2. Verbindungen mit Pentelid-Hanteln M2: AIII M6 und AII11M10 (A = Rb, Cs, Ba; M = Sb, Bi) / Compounds with Pentelide Dumbbells M2: AI11M6 and AII11M10 (A = Rb, Cs, Ba; M = Sb, Bi)
  3. Polysulfonylamine, CLXVII [1]. Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Dreipunktmuster als Bestandteil eines 2D-, eines zweifach verwobenen 2D- und eines 3D-Wasserstoffbrücken-Netzwerks / Polysulfonylamines, CLXVII [1]. Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Three-Point Pattern Integrated into a 2D, a Twofold Interwoven 2D, or a 3D Hydrogen-Bond Network
  4. Molecular Structure and Reactivity of Tri(1-cyclohepta-2,4,6-trienyl)amine, N(C7H7)3
  5. ScOH(CH3SO3)2, a Basic Methanesulfonate of Scandium with Chain Structure
  6. Calculated NMR Parameters (Chemical Shifts and Coupling Constants) of Cyclic C4H2 and C4H4 Molecules Containing Carbene Centers, and of Some of their Boron Analoga, Using Density Functional Theory (DFT)
  7. Atomvolumen, Packungsdichte und chemische Bindung in festem Iod unter Druck / Atomic Volume, Packing Density and Chemical Bonding in Solid Iodine under Pressure
  8. Secondary Interactions in Gold(I) Complexes with Thione Ligands. 1. Three Ionic Chlorides
  9. Chemical Composition and Antitumor Activities from Givotia madagascariensis
  10. A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium
  11. Synthese und Kristallstrukturanalyse eines 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepins / Synthesis and Crystal Structure Analysis of a 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepine
  12. Synthesis of Highly Flexible Difluorinated Cyclopropanoid Nucleoside Analogues
  13. A New Eudesmane Derivative from Leontodon tuberosus
  14. Structure of trans-Isoshinanolone in the Crystal and in Solution
  15. An Elegant Synthetic Route to 3-Cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles
  16. Boron Trifluoride Mediated Addition of Nucleophiles to endo- and exo-Substituted Norbornene Derivatives
  17. Fascicularones C and D, Tricyclo[5.4.0.02.5]undecane Sesquiterpenoids from the Liquid Culture of Naematoloma fasciculare
  18. A New Triterpenoid Saponin from Ononis spinosa and Two New Flavonoid Glycosides from Ononis vaginalis
https://doi.org/10.1515/znb-2004-0116
Keywords for this article
Remote Substituent Effects; endo/exo Selectivity; Regioselectivity; Nucleophilic Additions; π-Facial Selectivity

Articles in the same Issue

  1. The Low-Temperature Polymorph of Tetramethyldiphosphinebis( monoborane): Insight into the Stabilization of Different Rotational Isomers in the Solid State
  2. Verbindungen mit Pentelid-Hanteln M2: AIII M6 und AII11M10 (A = Rb, Cs, Ba; M = Sb, Bi) / Compounds with Pentelide Dumbbells M2: AI11M6 and AII11M10 (A = Rb, Cs, Ba; M = Sb, Bi)
  3. Polysulfonylamine, CLXVII [1]. Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Dreipunktmuster als Bestandteil eines 2D-, eines zweifach verwobenen 2D- und eines 3D-Wasserstoffbrücken-Netzwerks / Polysulfonylamines, CLXVII [1]. Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Three-Point Pattern Integrated into a 2D, a Twofold Interwoven 2D, or a 3D Hydrogen-Bond Network
  4. Molecular Structure and Reactivity of Tri(1-cyclohepta-2,4,6-trienyl)amine, N(C7H7)3
  5. ScOH(CH3SO3)2, a Basic Methanesulfonate of Scandium with Chain Structure
  6. Calculated NMR Parameters (Chemical Shifts and Coupling Constants) of Cyclic C4H2 and C4H4 Molecules Containing Carbene Centers, and of Some of their Boron Analoga, Using Density Functional Theory (DFT)
  7. Atomvolumen, Packungsdichte und chemische Bindung in festem Iod unter Druck / Atomic Volume, Packing Density and Chemical Bonding in Solid Iodine under Pressure
  8. Secondary Interactions in Gold(I) Complexes with Thione Ligands. 1. Three Ionic Chlorides
  9. Chemical Composition and Antitumor Activities from Givotia madagascariensis
  10. A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium
  11. Synthese und Kristallstrukturanalyse eines 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepins / Synthesis and Crystal Structure Analysis of a 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepine
  12. Synthesis of Highly Flexible Difluorinated Cyclopropanoid Nucleoside Analogues
  13. A New Eudesmane Derivative from Leontodon tuberosus
  14. Structure of trans-Isoshinanolone in the Crystal and in Solution
  15. An Elegant Synthetic Route to 3-Cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles
  16. Boron Trifluoride Mediated Addition of Nucleophiles to endo- and exo-Substituted Norbornene Derivatives
  17. Fascicularones C and D, Tricyclo[5.4.0.02.5]undecane Sesquiterpenoids from the Liquid Culture of Naematoloma fasciculare
  18. A New Triterpenoid Saponin from Ononis spinosa and Two New Flavonoid Glycosides from Ononis vaginalis
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