C. A. Grob, H. R. Pfaendler
1970
Citations
0
Influential Citations
14
Citations
Journal
Helvetica Chimica Acta
Abstract
In contrast to their acyclic analogues, 2-bromocyclohexa-1, 3-diene (11a) and 3-bromo-1, 5-dimethyl-cyclohexa-1, 3-diene (11b) do not react with silver ion, nor do they undergo solvolysis in 80% ethanol at temperatures up to 180°. The inertness to ionization of these cyclic bromodienes is attributed to steric inhibition of mesomerism involving the π electrons of the second double bond in the planar vinyl cation 12 and to the bent structure of this hypothetical intermediate.