Carbon Dioxide → 4-Vinyl-1-cyclohexene

Participants

Reaction Conditions

Reaction Steps

In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle: 0.25 grams (1.5 mmol) of ferric chloride, 0.3 grams (2.5 mg-atom) of tin powder and 0.3 grams (4.5 mmol) of sodium nitrite. The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF. The mixture was cooled with dry ice and 18.3 grams (339 mmol) of 1,3-butadiene added. This reaction mixture was heated to 75° C. with stirring. During this time, the original dark green solution changed in color to an orange-brown color. After 5 hours, the reaction was terminated and the reaction mixture allowed to cool to room temperature and stand for 1 day. Pressure on the reactor was still at 25 psig indicating there had been little, if any, conversion of 1,3-butadiene to the dimer. The results of this run indicate that one does not obtain dimerization of 1,3-butadiene to 4-vinylcyclohexene if one attempts to form the iron nitrosyl halide simultaneously with the dimerization.

Provenance & Evidence