Dergiler / Turkish Journal of Chemistry / 2004 / Cilt: 28 - Sayı: 6

Bromination of Tricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraene Derivatives: Electronic and Neighboring Group Effects on Bromination

Sayfa
715–724
DOI
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Özet

The bromination reaction of tricyclo[7.2.1.02,7]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.

Abstract

The bromination reaction of tricyclo[7.2.1.02,7]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.

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