Synthesis and structure elucidation of bromination products from dibromohomobenzonorbornadienes: high temperature bromination - Part 17

Date

2005-01-01

Author

Kazaz, C
Dastan, A
Balcı, Metin

Metadata

Show full item record

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

Item Usage Stats

98
views

0
downloads

The electrophilic addition of bromine to dibromohomobenzonorbornadiene derivatives at -45 +/- 5degreesC led to the formation of the rearranged and non-rearranged tetrabromides in a ratio of 6:4. However, high-temperature bromination of the same system in CCl4 at 77degreesC produced only non-rearranged products. The formation mechanism of the isomers and the role of the substituent on the rearrangement is discussed. The structure elucidation of the isomeric tetrabromides was achieved from NMR spectral data. The agreement between the calculated dihedral angles and the measured coupling constants is especially excellent. The),gauche effect is discussed. Copyright (C) 2004 John Wiley Sons, Ltd.

Subject Keywords

General Materials Science, General Chemistry

URI

https://hdl.handle.net/11511/57182

Journal

MAGNETIC RESONANCE IN CHEMISTRY

DOI

https://doi.org/10.1002/mrc.1490

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis and characterization of a new soluble conducting polymer and its electrochromic device Varis, Serhat; Ak, Metin; Tanyeli, Cihangir; Akhmedov, Idris Mecidoglu; Toppare, Levent Kamil (Elsevier BV, 2006-12-01) A mixture of isomers 2,5-di(4-methyl-thiophen-2-yl)-1-(4-nitrophenyl)-1H-pyrrole, 2-(4-methyl-thiophen-2-yl)-5-(3-methyl-thiophen-2-yl)1-(4-nitrophenyl)-1H-pyrrole and 2,5-di(3-methyl-thiophen-2-yl)-1-(4-nitrophenyl)-1H-pyrrole (Me-SNS(NO2)) were synthesized. Resulting monomers were polymerized chemically, producing soluble polymers in common organic solvents. The average molecular weight has been determined by gel permeation chromatography (GPC) as Mn = 5.6 x 10(3) for the chemically synthesized polymer. T...
Synthesis, Characterization and Optoelectrochemical Properties of Poly(2,5-di(thiophen-2-yl)-1-(4-(thiophen-3-yl)phenyl)-1H-pyrrole-co-EDOT) Turac, Ersen; Sahmetlioglu, Ertugrul; Toppare, Levent Kamil; Yuruk, Huseyin (Informa UK Limited, 2010-01-01) A new polythiophene derivative was synthesized by electrochemical oxidative polymerization of 2,5-di( thiophen-2-yl)-1-(4-(thiophen-3-yl) phenyl)-1H-pyrrole (TTPP). The structure of the monomer was evaluated by H-1-NMR and FT-IR. The polymer (P(TTPP)) and its co-polymer with 3,4-ethylenedioxythiophene (P(TTPP-co-EDOT)) were synthesized via potentiostatic electrochemical polymerization. The resulting polymers were characterized by cyclic voltammetry (CV), FT-IR, SEM and UV-Vis spectroscopy, and conductivity ...
Atom transfer rearrangement radical polymerization of diammine-bis(2,4,6-trihalophenolato)copper(II) complexes in the solid state Goekagac, Guelsuen; Sonsuz, Muammer; Sen, Fatih; Kisakuerek, Duygu (Walter de Gruyter GmbH, 2006-10-01) The synthesis of the poly(dichloro- or dibromophenylene oxide)s was achieved by the thermal decomposition of diammine-bis(2,4,6-trihalophenolato)copper(II) complexes in the solid state by atom transfer rearrangement radical polymerization. The thermal decomposition was performed either at different temperature ranges, 110-250 degrees C, for 3 h, or at the maximum conversion temperature for different time intervals, 3-48 h. Maximum yields of polymers were obtained at 190 degrees C and 3 h. The polymers were ...
Synthesis, crystal structure and characterization of new transition metal compounds of bromophenols: Bis(2,4,6-tribromophenolato) di(N-methylimidazole)M(II) (M=Co, Cu) Camurlu, P; Yılmaz, Ayşen; Tatar, L; Kisakurek, D; Ulku, D (Wiley, 2005-03-01) Bis(2,4,6-tribromophenolato)di(N-methyl imidazole)M(II), where M stands for cobalt and copper metals, was synthesized via reaction of the corresponding metal sulphate and 2,4,6-tribromophenolate in aqueous media in the presence of N-methyl imidazole and sodium hydroxide. Although various crystallization procedures were applied only cobalt complex was obtained as single crystals. The Co(II) ion has a distorted octahedral enviroment involving two O atoms and two N atoms of the Bis(2,4,6-tribromopbenolato)di(N...
Theoretical and experimental considerations on poly(dihalophenylene oxide)s Kisakürek, Duygu (Wiley, 1988) The decomposition of copper(II) trihalophenoxides in acetonitrile yields poly(dihalophenylene oxide)s. A 1H n.m.r. study has shown that a bromine atom in the 4‐position of the trihalophenoxides results in polymers having higher linearity. Various dynamic and static methods, within the framework of Hückel molecular orbital theory, have been used to explain the product distribution.

Citation Formats

C. Kazaz, A. Dastan, and M. Balcı, “Synthesis and structure elucidation of bromination products from dibromohomobenzonorbornadienes: high temperature bromination - Part 17,” MAGNETIC RESONANCE IN CHEMISTRY, pp. 75–81, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57182.