Acetylenedicarbonitrile → HCID 178444402, compound

Participants

Reaction Steps

9.5 g of 1-(trans-4-pentylcyclohexyl)-3,5-trans-nonadiene were dissolved in 62 ml of tetrahydrofuran in a round flask and treated with 14 mg of hydroquinone. A solution of 3.2 g of dicyanoacetylene in 18 ml of tetrahydrofuran was subsequently added by means of a pipette and the pipette was rinsed twice with 9 ml of tetrahydrofuran each time. The mixture was stirred at room temperature for 2.5 hours and then overnight at 40°-45° C. (bath temperature) under nitrogen. The dark brown solution was thereafter concentrated in vacuo. The resulting dark brown oil (10.9 g) was chromatographed on silica gel using hexane, hexane/toluene (volume ratio 1:1) and toluene, there being obtained 4.2 g of unreacted 3-cis, 5-trans-diene as a colourless oil and 7.4 g of 1,2-dicyano-3-[2-(trans-4-pentylcyclohexyl)ethyl]-6-propyl-1,4-cyclohexadiene as a slightly yellowish oil.

Provenance & Evidence