反应详情

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).

1. temperatureThe reaction mixture was refluxed
2. washwashed twice with water
3. dry with materialThe organic layer was dried with MgSO4
4. customevaporated
5. customAn analytically pure sample could be obtained by crystallization from acetone and sublimation (115° C./0.002 mm)