Bromination of 2,3-dibromobenzobarrelene at 77 °C was studied and 2,3,5-tribromobenzobarrelene was obtained in high yield. All compounds were characterised properly, especially by NMR spectra.
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18.
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HBr elimination takes place via syn-elimination in molecule 34. Gronert explained that cis-elimination could occur more readily than trans-elimination in bicyclic systems; S. Gronert. J. Org. Chem. 1994, 59, 7046.