Tetrahydrofuran → Phenyl-t-butylacetylene

Participants

Reaction Conditions

Reaction Steps

A solution containing W(CCMe3)(Cl3)(OPEt3) (0.43 g, 0.866 mmol) and diphenylacetylene (0.18 g, 1.0 mmol) in 2 ml of tetrahydrofuran was heated to 60° C. for 2 hours. During this time, the color of the reaction mixture changed from blue to green. Phenyl-t-butylacetylene (100% yield versus tungsten) was observed in the reaction mixture by gas chromatography. The reaction mixture was filtered and PMe3 (0.30 ml, 3.0 mmol) was added by syringe. The color of the solution turned yellow, and after the addition of 2 ml pentane, yellow crystals precipitated from solution. The product was collected by filtration and was recrystallized from a mixture of tetrahydrofuran and pentane at -30° C.; total yield 0.47 g (89%) W(CPh)Cl3 (PMe3)3.

Provenance & Evidence