Miller L L, Narang R S
Science. 1970 Jul 24;169(3943):368-70. doi: 10.1126/science.169.3943.368.
Photolysis of mixtures of certain alkyl halides and aromatic amines produces dehalogenation of the halide. These reactions involve a photoinduced charge transfer from the amine to the halide. Photolysis of tritolylamine and carbon tetrachloride produces tritolylaminium chloride. Photolysis of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT) and diethylaniline at 3100 angstroms yields 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (DDE), 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane (DDD), p,p'-dichlorobenzophenone (DDCO), and hydrogen chloride. Photolysis of DDT does not occur unless an inducer which has a low ionization potential, such as diethylaniline, is present. The DDT-diethylaniline mixture is stable in the dark, and the induced photolysis is not affected by triplet quenchers.
某些卤代烷与芳香胺的混合物经光解会使卤化物发生脱卤反应。这些反应涉及光诱导的从胺到卤化物的电荷转移。三苯胺与四氯化碳光解生成三苯铵氯化物。1,1,1 - 三氯 - 2,2 - 双(对氯苯基)乙烷(滴滴涕,DDT)与二乙苯胺在3100埃波长下光解生成1,1 - 二氯 - 2,2 - 双(对氯苯基)乙烯(DDE)、1,1 - 二氯 - 2,2 - 双(对氯苯基)乙烷(DDD)、对,对'-二氯二苯甲酮(DDCO)和氯化氢。除非存在具有低电离势的诱导剂,如二乙苯胺,否则滴滴涕不会发生光解。滴滴涕 - 二乙苯胺混合物在黑暗中稳定,且诱导光解不受三线态猝灭剂影响。