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- Title
Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel.
- Authors
EŞSİZ, Selçuk; ŞENGÜL, Mehmet Emin; ŞAHİN, Ertan; DAŞTAN, Arif
- Abstract
The bromination reaction of dihydrobenzobarrelene under different conditions was studied. The bromination reaction of dihydrobenzobarrelene with molecular bromine gave only aWagner-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.
- Subjects
BROMINATION; CYCLIC compounds; ETHYLENE dibromide; ORGANIC synthesis; CARBOCATIONS; REARRANGEMENTS (Chemistry); SILICA gel; CHEMICAL reactions; HIGH temperatures
- Publication
Turkish Journal of Chemistry, 2011, Vol 35, Issue 4, p587
- ISSN
1300-0527
- Publication type
Article
- DOI
10.3906/kim-1101-991