Carbon Tetrachloride → 4,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

반응식

C[C:2]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:8][C:7](C)=[N:6]3)[N:3]=1.ClN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:55]([Cl:59])([Cl:58])([Cl:57])Cl.[CH:60]([Cl:63])([Cl:62])[Cl:61]>>[Cl:61][C:60]([Cl:63])([Cl:62])[C:7]1[CH:8]=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[C:5](=[C:4]3[C:13](=[CH:12][CH:11]=2)[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:2]([C:55]([Cl:59])([Cl:58])[Cl:57])=[N:3]3)[N:6]=1

참가 물질

반응물 5

HCID 5943Carbon Tetrachloride

HCID 6212Chloroform

HCID 7187Benzoyl Peroxide

HCID 31398Chlorosuccinimide

HCID 65149Bathocuproine

생성물 1

HCID 149578744,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

실험 절차

A mixture composed of 2,9,-dimethyl-4,7-diphenyl-1,10-phenanthroline (4.0 g, 0.011 mole), N-chlorosuccinimide (9.0 g, 0.067 mole), benzoyl peroxide (0.011 g) and 96 ml carbon tetrachloride was stirred for 6 hr in an oil bath at 90°. After standing overnight at 4° C., crystals of succinimide were removed by filtration. The solvent was removed from the filtrate by vacuum evaporation to produce a light yellow solid which was then dissolved in chloroform. The organic layer was washed with saturated sodium carbonate solution and dried over anhydrous magnesium sulfate. Removal of solvent by vacuum evaporation yielded the white solid product. Yield=6.1 g (97%). Mp=286°-289°. IR 3020-3080, 1620, 1570, 1550, 1490, 1445, 1405, 1360, 1220, 1040, 930, 895, 835, 800, 780, 760, 735, 700, 620 cm-1. 60 MHz proton NMR in CDCl3 δ7.55 singlet (10 protons), δ8.05 singlet (2 protons), δ8.3 singlet (2 protons).