Methylphenylacetylene → Diphenylacetylene

Participants

Reaction Conditions

Reaction Steps

In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol) and molecular sieve 5 Å (1.0 g) was suspended in dry toluene (5 mL) and the mixture was heated to 80° C. After 30 min, 1-phenyl-1-propine (116.2 mg, 1.00 mmol) was added, the reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 88.2 mg of tolane (99%) were isolated as a white solid, the spectroscopic and analytical data were identical to those of a commercial sample. M.p.=59-61° C.

Provenance & Evidence