Naama Zuaretz, O. Golan, S. Biali
Mar 1, 1991
Citations
0
Influential Citations
9
Citations
Journal
Journal of Organic Chemistry
Abstract
Decakis(bromomethyl)biphenyl (3) has been prepared by reaction of decamethylbiphenyl with Br 2 /CCl 4 in the presence of tetrabutylammonium bromide as catalyst. MM2(85) calculations on 3 indicate that some conformations with disrupted «up-down» alternation of the CH 2 Br groups are favored over the all-alternate up-down form. It is suggested that this conformational shift is the result of the mutual steric interactions between arms of different moieties, and that syn interactions between m-and p-CH 2 Br groups operate in order to avoid bromine contacts between ortho groups at different rings. The barrier for Ar-CH 2 Br rotation was estimated from dynamic NMR data