N,N,N',N'-Tetramethylethylenediamine → 9,9'-(Buta-1,3-diyne-1,4-diyl)dianthracene

反応式

[C:1]([C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)#[CH:2].CN(C)[CH2:19][CH2:20]N(C)C>CC(C)=O.[Cu]Cl>[CH:5]1[C:4]2[C:9](=[CH:10][C:11]3[C:16]([C:3]=2[C:1]#[C:2][C:7]#[C:6][C:5]2[C:4]4[C:3]([CH:1]=[C:20]5[C:19]=2[CH:15]=[CH:14][CH:13]=[CH:12]5)=[CH:16][CH:11]=[CH:10][CH:9]=4)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1

参加物

実験手順

15 g (0.074 mol) of 9-ethynyl anthracene, 0.36 g (3.7 mmol) copper(I) chloride, 0.43 g (3.7 mmol) of N,N,N′,N′-tetramethylethylenediamine were put into a 500 ml round-bottomed flask equipped with a stirrer, and then dissolved in 200 ml of acetone. The resulting mixture was then vigorously stirred for two hours while purging oxygen gas, to give red-colored solid. After the reaction was completed, the solvent was mostly removed with a small amount remaining. The residue was then precipitated in 5% aqueous hydrochloric acid to obtain red-colored solid. The solid was filtered, washed sufficiently with water and ethanol, and then recrystallized from ethyl acetate, to give red-colored crystal. The red-colored crystal was recovered and then sufficiently dried in a vacuum oven at 40° C., to give 13 g (87.2% yield) of the desired product having a melting point of 280-282° C.