反应详情

To stirred, refluxing mixture of 100.0 grams (1.22 mole) of cyclohexene and 0.037 gram (0.0001 mole) of cupric acetylacetonate was fed 22.7 grams (0.14 mole) of dimethyl diazomalonate over a 25-hour period by means of a syringe pump. Refluxing was continued for an additional 8 hours after which distillation of the reaction mixture was begun, employing a small Vigreux column. After removing about 32 grams of cyclohexene overhead, to a head temperature of 80° C., the residue was allowed to cool. The solidified residue was worked up by flash column chromatography on silica gel to give 17.53 grams (0.08 mole) of dimethyl bicyclo[4.1.0]heptane-7,7-dicarboxylate having a melting point of 83° C.-86° C. Elemental analysis of the product indicated the following:

1. temperaturerefluxing
2. customover a 25-hour
3. temperatureRefluxing
4. distillationafter which distillation of the reaction mixture
5. customAfter removing about 32 grams of cyclohexene overhead
6. customto a head temperature of 80° C.
7. temperatureto cool