o-Bis(bromomethyl)benzene → 1-Tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-ylidene-pyrrolidinium bromide

Participants

Reaction Steps

1,2-Bis-bromomethyl-benzene (66.4 g, 0.25 mol) was added to a mixture of 1-cyclopent-1-enyl-pyrrolidine (29.4 g, 0.25 mol) and Hünig's base (87 mL, 0.50 mol) in MeCN (200 mL) with vigorous stirring. An exothermic reaction ensued, bringing the mixture to reflux. The mixture was refluxed for 16 h, cooled, the product was filtered off and washed with MeCN to give the pure title compound as a white crystalline solid (48.14 g, 60%). 1H NMR (d6-DMSO, 360 MHz) δ 7.29-7.22 (4 H, m, aromatic), 4.16-4.11 (2 H, m, CH—N+), 4.04-3.99 (2 H, m, CH—N+), 3.60 (2 H, bs, bridgehead CH), 3.05 (4 H, d, benzylic), 2.17-2.05 (4 H, m, N+—C—CH2), 1.92-1.88 (2 H, m), 1.25-1.20 (2 H, m). m/z 240 (M+).

Provenance & Evidence