[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(/C=C\C2C=CC=CC=2)C=CC=CC=1.C1(/C=C/C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=11.34 g (7.5 mmol) of diphenylacetylene (1), 4.01 mL (225 mmol) of distilled water and stainless steel balls (25 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 6 hours at 650 rpm (reversed every 30 minutes). After the lapse of 6 hours, 200 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The filtrate was concentrated, thereby providing reaction products. The confirmation by 1H-NMR thereof revealed that a mixture of cis-1,2-diphenylethylene (26), trans-1,2-diphenylethylene (27) and 1,2-diphenylethane (2) was obtained at a mixing ratio of 92/0/8. The yield was 92%. The reaction is expressed by the following scheme.
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