Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel
Özet
The bromination reaction of dihydrobenzobarrelene under different conditions was studied. The bromination reaction of dihydrobenzobarrelene with molecular bromine gave only a Wagner-Meerwein rearrangement product by aryl and alkyl migration. Its high-temperature bromination reaction resulted in the formation of normal addition products besides rearrangement products. The bromination reaction of the alkene with 1,2- dibromotetrachloroethane (DBTCE) gave a non-rearrangement product as the sole product. The synthesis and bromination reaction of 2- bromodihydrobenzobarrelene was also studied. An unexpected Wagner-Meerwein rearrangement was observed on silica gel during the column chromatography of isomeric tribromides. Herein, we report the results of the synthesis, and the X-ray crystal structures and the possible mechanism of processes are discussed.
Atıf için künye
Essiz, S., SENGUL, M. E., Şahin, E., & Daştan, A. (2011). Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel. TURKISH JOURNAL OF CHEMISTRY, 35(4), 587–598. https://doi.org/10.3906/kim-1101-991
BibTeX
@article{essiz2011-66791,
author = {Essiz, Selçuk and SENGUL, Mehmet Emin and Şahin, Ertan and Daştan, Arif},
title = {Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel},
journal = {TURKISH JOURNAL OF CHEMISTRY},
year = {2011},
volume = {35},
number = {4},
pages = {587--598},
issn = {1300-0527},
doi = {10.3906/kim-1101-991},
url = {https://akademik.atauni.edu.tr/yayinlar/66791-bromination-of-23-dihydrobenzobarrelene-and-synthesis-of-its-mono-and-dibromide}
}