Chlorosuccinimide → HCID 86741865, compound

Participants

Reaction Steps

To a solution of 200 mg (0.82 mmol) of bicyclo[3,3,1]nonylidene-bicyclo[3,3,1]nonane (formula 17) in 20 cm3CH2Cl2, 115 mg (0.86 mmol) N-chlorosuccinimide was added. The reaction mixture was refluxed and stirred for 1 hour, and CH2Cl2 was added to dilute the reaction mixture. The organic layer was washed twice with water, dried with MgSO4 and evaporated. The yield of 4-eq.-chlorobicyclo[3,3,1]nonylidene-bicyclo[3,3,1]nonane was 190 mg. Purification was effected via chromatography (hexane, Al2O3) and sublimation (45° C./0.01 mm), melting point 50.53° C., 1H NMR (CDCl3) δ 4.4-3.9 (m, 1H); 3.1 (br s, 1H): 2.85 (br s, 3H); 2.5-1.2 (br, 22H); 13C NMR (CDCl3) δ 136.8 (s); 129.7 (s); 66.0 (d) and lines between 39.7 and 21.7; mass m/e 278:280 (3:1 ); exact mass: calculated 278.180; found 278.182.

Provenance & Evidence