Methylphenylacetylene → Diphenylacetylene

HRID 879941Notes

Reaction equation

[C:1]1([C:7]#[C:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[C:1]1([C:7]#[C:8][C:9]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a dry 10 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (50.0 μmol, 58.1 mg) and MnCl2 (50.0 μmol, 6.3 mg) were suspended in 2.5 mL of toluene. After addition of 1-phenyl-1-propine (500 μmol, 58.1 mg), the reaction solution was stirred for 24 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 column chromatography (hexane). 41.6 mg of tolane (93%) were isolated as white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C.

Workup

filtrationwas filtered
temperatureafter cooling over a short silica gel column
concentrationThe filtrate was concentrated
customthe residue was purified by column chromatography (hexane)

Sources & evidence

ORD record: ord-b16dbac1f94648f599c700d364dde731
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993470B2

Reaction notes

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