N-bromobutanimide → Bromoadamantylideneadamantane

Participants

Reaction Steps

To a solution of 3 mmols (804 mg) adamantylideneadamantane in 40 cm3CH2Cl2, 6.6 mmols (1.175 g) N-bromosuccinimide was added. The reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was diluted with CH2Cl2 and washed twice with water and a saturated Na2S3O3 -solution. The organic layer was dried with MgSO4 and evaporated. The yield of 4-eq.-bromoadamantylideneadamantane having formula 20 was 1.05 g (97%). An analytically pure sample could be obtained by crystallization from acetone and sublimation (115° C./0.002 mm); melting point 130.5-131.5° C. 1H NMR (CDCl3); δ 4.4 (br s, 1H); 3.05 (br s, 1H); 2.8 (br s, 3H); 2.6-1.2 (br m, 22H); 13C NMR (CDCl3); δ 136.9 (s); 131.0 (s); 63.8 (d) and 12 signals between 39.9 and 27.6. Analysis, calculated: 69.16 C; 7.84 H; 23.01 Br; found: 69.21 C; 7.82 H; 22.99 Br. Mass m/e 346:348 (1:1).

Provenance & Evidence