Novel aromatic systems. Part VI. Some aspects of the bromination of indane and 2,3-dimethylfluorenone
Abstract
N-Bromosuccinimide (4 mol.) reacts with indane to give 1,3,3-tribromoindene and 1,2,3-tribromoindene. Hydrolyses of these give 3-bromoinden-1-one, 2,3-dibromoinden-1-one, 2,3-dibromoinden-1-ol and 1-acetoxy-2,3-dibromoindene while reactions of the tribromoindenes with collidine gives 4,5,7-tribromodibenzo[b,i]fulvalene. Sulphuric acid converted 2,3-dibromoinden-1-one into 2,2-dibromoindane-1,3-dione and 1,2,3-tribromoindene into 2,2,3-tribromoinden-1-one. 2,3-Bisdibromomethylfluoren-9-one has been synthesised and converted into several products. 4′,5′-(3-Methylcyclopenteno)-3′,6′-dihydroxy-1,2-benzocycloheptene-3,7-dione has been prepared.