Bromination of Tricyclo[^{2,7}]dodeca-2,4,6,10-tetraene Derivatives: Electronic and Neighboring Group Effects on Bromination


Abstract: The bromination reaction of tricyclo[^{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.

Keywords: Bromination, Wagner-Meerwein Rearrangement (W.M.R.), Polybromides, Neighboring Group Effect

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