Bromination of tricyclo $[7.2.1.0^{2,7}]$ dodeca-2,4,6,10-tetraene derivatives: electronic and neighboring group effects on bromination

Abstract

The bromination reaction of tricyclo $[7.2.1.0^{2,7}]$ dodeca-2,4,6,10-tetraene derivatives was studied. The bromination of 9 gave only rearranged products 12 and 13, while the bromination of 8 with molecular bromine formed both rearranged 12 and non-rearranged products 15 and 16. The possible role of a substituent in the rearrangements was examined. All compounds were characterized properly, in particular by NMR spectra and chemical transformation.