Boron trifluoride mediated addition of nucleophiles to endo- and exo-substituted norbornene derivatives

Date

2004-01-01

Author

İŞLEYEN, Alper
SAYRAÇ, Tuğmaç
Doğan, Özdemir

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

141
views

0
downloads

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.

Subject Keywords

Remote substituent effects, Endo/exo selectivity, Regioselectivity, Nucleophilic additions, Pi-facial selectivity

URI

https://hdl.handle.net/11511/55438

Journal

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Rhodium(0) nanoparticles supported on hydroxyapatite nanospheres and further stabilized by dihydrogen phosphate ion: A highly active catalyst in hydrogen generation from the methanolysis of ammonia borane Ozhava, Derya; Özkar, Saim (Elsevier BV, 2015-09-07) Rhodium(0) nanoparticles, supported on nanosized hydroxyapatite (Rh(0)/nanoHAP), were prepared by ion exchange of Rh+3 ions with Ca+2 ions of hydroxyapatite, followed by reduction of the resulting Rh+3/nanoHAP precatalyst during the catalytic methanolysis of ammonia borane (AB) in the presence of tetrabutylammonium dihydrogen phosphate (TBAP) at room temperature. Rh(0)/nanoHAP were characterized by a combination of advance analytical techniques including ICP-OES, XRD, TEM, EDX, XPS, ATR-IR and N-2 adsorptio...
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: synthesis, in vitro evaluation, and molecular docking studies Esiyok, Peruze Ayhan; Seven, Ozlem; Eymur, Guluzar; Tatar, Gamze Bora; DAYANGAÇ ERDEN, DİDEM; YELEKÇİ, Kemal; YURTER, HAYAT; Demir, Ayhan Sıtkı (The Scientific and Technological Research Council of Turkey, 2014-01-01) New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl or morpholine. These compounds have been shown to possess promising histone deacetylase inhibition activities via in vitro fluorometric assay and molecular docking studies.
Molecular recognition of poly(A) by small ligands: an alternative method of analysis reveals nanomolar, cooperative and shape-selective binding Persil Çetinkol, Özgül (Oxford University Press (OUP), 2009-02-01) A few drug-like molecules have recently been found to bind poly(A) and induce a stable secondary structure (T(m)approximate to 60 degrees C), even though this RNA homopolymer is single-stranded in the absence of a ligand. Here, we report results from experiments specifically designed to explore the association of small molecules with poly(A). We demonstrate that coralyne, the first small molecule discovered to bind poly(dA), binds with unexpectedly high affinity (K(a) >10(7) M(-1)), and that the crescent sh...
Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde Demir, Ayhan Sıtkı; Sesenoglu, O; Dunkelmann, P; Muller, M (American Chemical Society (ACS), 2003-06-12) Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
Poly(4-styrenesulfonic acid-co-maleic acid) stabilized cobalt(0) nanoparticles: A cost-effective and magnetically recoverable catalyst in hydrogen generation from the hydrolysis of hydrazine borane Karahan, Senem; Özkar, Saim (2015-02-09) Herein, we report the in situ generation, isolation and characterization of cobalt(0) nanoparticles, stabilized by poly(4-styrenesulfonic acid-co-maleic acid), PSSMA, and their catalytic activity in the hydrolysis of hydrazine borane (HB). Cobalt(0) nanoparticles having average particle size of 3.1 +/- 0.5 nm were prepared by in situ reduction of cobalt(II) chloride in aqueous solution of hydrazine borane in the presence of PSSMA, isolated magnetically from the catalytic reaction solution using a magnet, an...

Citation Formats

A. İŞLEYEN, T. SAYRAÇ, and Ö. Doğan, “Boron trifluoride mediated addition of nucleophiles to endo- and exo-substituted norbornene derivatives,” ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, pp. 109–118, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/55438.