HIGH-TEMPERATURE BROMINATION .5. FUNCTIONALIZATION OF BENZONORBORNADIENE - HIGH-TEMPERATURE BROMINATION AND ELECTROCHEMICAL OXIDATION
Özet
The electrophilic addition of bromine to benzonorbornadiene (1) at 10 degrees C led in high yield to the formation of 2-exo-7-anti-dibromide 2. However, high-temperature bromination in decalin at 150 degrees C resulted in the formation of five products, 2-6, consisting of non-rearranged and rearranged products in a ratio of 8:2. Conducting the bromination reaction in the presence of a free radical inhibitor like 2,4,6-tri-tert-butylphenol suppressed the formation of the non-rearranged products. This very strongly supports the assumption that there is a competition between radical and ionic reactions. Anodic oxidation of benzonorbornadiene was investigated. Electrolysis of benzonorbornadiene in different solvents resulted in the formation of 2,7-disubstituted benzonorborn-5-ene derivatives, 8-11, in good yields.
Atıf için künye
Daştan, A., DEMIR, Ü., & BALCI, M. (1994). HIGH-TEMPERATURE BROMINATION .5. FUNCTIONALIZATION OF BENZONORBORNADIENE - HIGH-TEMPERATURE BROMINATION AND ELECTROCHEMICAL OXIDATION. JOURNAL OF ORGANIC CHEMISTRY, 59(22), 6534–6538. https://doi.org/10.1021/jo00101a011
BibTeX
@article{dastan1994-70712,
author = {Daştan, Arif and DEMIR, Ümit and BALCI, M},
title = {HIGH-TEMPERATURE BROMINATION .5. FUNCTIONALIZATION OF BENZONORBORNADIENE - HIGH-TEMPERATURE BROMINATION AND ELECTROCHEMICAL OXIDATION},
journal = {JOURNAL OF ORGANIC CHEMISTRY},
year = {1994},
volume = {59},
number = {22},
pages = {6534--6538},
issn = {0022-3263},
doi = {10.1021/jo00101a011},
url = {https://akademik.atauni.edu.tr/yayinlar/70712-high-temperature-bromination-5-functionalization-of-benzonorbornadiene-high}
}