COMPETITIVE REARRANGEMENTS .2. NEOPENTYLIC VERSUS SKELETAL REARRANGEMENT IN THE REACTION OF T-BUTIL-DIBENZOBICYCLO[2.2.2] OCTATRIENE WITH BROMINE

Authors
GOTTLIEB H BRAVERMAN S IONICA I FILIP P BADEA F DINULESCU IG
Citation
H. Gottlieb et al., COMPETITIVE REARRANGEMENTS .2. NEOPENTYLIC VERSUS SKELETAL REARRANGEMENT IN THE REACTION OF T-BUTIL-DIBENZOBICYCLO[2.2.2] OCTATRIENE WITH BROMINE, Revue Roumaine de Chimie, 37(11-12), 1992, pp. 1219-1223
Citations number
8
Categorie Soggetti
Chemistry
Journal title
Revue Roumaine de Chimie → ACNP
ISSN journal
00353930
Volume
37
Issue
11-12
Year of publication
1992
Pages
1219 - 1223
Database
ISI
SICI code
0035-3930(1992)37:11-12<1219:CR.NVS>2.0.ZU;2-K
Abstract
t-Butyl-dibenzobicyclo [2.2.21 octatriene (8) reacts with bromine yiel ding as a single reaction product the rearranged dibromo-derivative 15 . The formation of 15 from 8 involves a 12.2.2] --> [3.2.11 skeletal r earrangement. Under the same conditions, 1 (the carbomethoxy derivativ e of 8)undergoes a neopentylic rearrangement. Mechanistic aspects of t hese reactions are discussed.