Bromination of an N-carbethoxy-7-aza-2,3-benzonorbornadiene and synthesis of N-carbethoxy-7-aza-2,3-dibromo-5,6-benzonorbornadiene: High temperature bromination. Part 14

Date

2002-10-28

Author

Tutar, 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

38
views

0
downloads

The electrophilic addition of bromine to an N-carbethoxy-7-aza-2,3-benzonorbomadiene at 0degreesC led in high yield to the formation of rearranged dibromides. However, high-temperature bromination of N-carbethoxy-7-aza-2,3-benzonorbomadiene in carbon tetrachloride at 77degreesC while irradiating, gave exclusively non-rearranged products. From the elimination of these non-rearranged products, N-carbethoxy4-bromo-7-aza-2,3-benzonorbomadiene was obtained as the sole product. Similarly, bromination of monobromide N-carbethoxy-4-bromo7-aza-2,3-benzonorbomadiene at 77degreesC yielded non-rearranged tribromides. The dehydrobromination of these tribromides provided the N-carbethoxy-5,6-dibromo-7-aza-2,3-benzonorbomadiene in high yield, which is a synthon for trimerization reaction.

Subject Keywords

Rearrangements, Aza compounds, Bicyclic heterocyclic compounds

URI

https://hdl.handle.net/11511/57177

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/s0040-4020(02)01150-x

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls Demir, Ayhan Sıtkı; Reis, O; Emrullahoglu, M (2003-01-24) The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields are better than those from similar, previously described methods. Arylboronic acids carrying sensitive functional groups also work efficiently.
Use of purified and modified bentonites in linear low-density polyethylene/organoclay/compatibilizer nanocomposites Seyidoglu, Tijen; Yılmazer, Ülkü (2012-05-05) Polyethylene-based ternary nanocomposites were prepared with different clay structures, obtained by the modification of purified Resadiye bentonite as the reinforcement, a random terpolymer of ethylene, butyl acrylate, and maleic anhydride with the trade name Lotader3210 as the compatibilizer, and linear low-density polyethylene (LLDPE) as the polymer matrix in an intensive batch mixer. The quaternary ammonium/phosphonium salts used for the modification of bentonite were dimethyldioctadecyl ammonium (DMDA) ...
Flame retardancy effects of zinc borate and nanoclay in ABS, and boron compounds in PET Özkaraca, Ayşe Çağıl; Kaynak, Cevdet; Department of Metallurgical and Materials Engineering (2011) In this thesis there were two main purposes, the first one being to investigate effects of zinc borate (ZB) on the flammability behavior of ABS when used with and without a traditional brominated flame retardant (BFR) / antimony trioxide (AO) system. The second purpose was to investigate contribution of nanoclays (NC) to the flame retardancy performance of the same traditional BFR compound with various combinations of AO and ZB again in ABS matrix. For these purposes, materials were melt compounded by using...
Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane Demir, Ayhan Sıtkı; Igdir, AC; Mahasneh, AS (1999-10-15) An efficient oxidative coupling of thiols to give disulfides via thionitrite (S-nitrosothiol) intermediate is described using trichloronitromethane as an efficient reagent in organic solvents and water. Cysteine and glutathione are converted into the corresponding disulfides in water in high yields.
ELECTROPHILIC SUBSTITUTION IN INDOLES .18. HAMMETT CORRELATIONS OF THE COUPLING OF ARYL DIAZONIUM TETRAFLUOROBORATES WITH INDOLE ABDULLAH, MI; JACKSON, AH; LYNCH, PP; RECORD, KAF (1990-01-01) Hammett plots for the coupling of a series of substituted aryldiazonium salts with indole and 3-methylindole show linear relationships thus confirming that the reactions are typical aromatic electrophilic substitutions.

Citation Formats

A. Tutar and M. Balcı, “Bromination of an N-carbethoxy-7-aza-2,3-benzonorbornadiene and synthesis of N-carbethoxy-7-aza-2,3-dibromo-5,6-benzonorbornadiene: High temperature bromination. Part 14,” TETRAHEDRON, pp. 8979–8984, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57177.