Hydroquinone → Chloroadamantylidene adamantane

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To a solution of 1 mmol (268 mg) adamantylidene adamantane having the formula 19 in 20 cm3CH2Cl2, 1.05 mmoles (140 mg) N-chlorosuccinimide was added. The reaction mixture was stirred at room temperature for 1 hour, diluted with CH2Cl2, and washed twice with water. The organic layer was dried with MgSO4 and evaporated. The yield of 4-eq.-chloroadamantylideneadamantane was 300 mg (98%), melting point: 142°-143° C. (literature: 144°-145° C.). 1H NMR (CDCl3): δ 4.15 (br s, 1H); 3.05 (br s 1H); 2.8 (br s, 3H); 2.6-1.15 (br m, 22H) ppm. When 0.1 mmol hydroquinone was added to the solution, exactly the same reaction occurred, and the product could be isolated in virtually the same quantitative yield.

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