Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel

Authors

SELÇUK EŞSİZ
MEHMET EMİN ŞENGÜL
ERTAN ŞAHİN
ARİF DAŞTAN

DOI

10.3906/kim-1101-991

Abstract

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.

Keywords

Bromination, benzobarrelene, Wagner-Meerwein rearrangement

First Page

587

Last Page

598

Recommended Citation

EŞSİZ, SELÇUK; ŞENGÜL, MEHMET EMİN; ŞAHİN, ERTAN; and DAŞTAN, ARİF (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: Vol. 35: No. 4, Article 7. https://doi.org/10.3906/kim-1101-991
Available at: https://journals.tubitak.gov.tr/chem/vol35/iss4/7