Photoinduced electron transfer chemistry of 9-methylanthracene. Substrate as both electron donor and acceptor in the presence of the 1-ethyl-3-methylimidazolium ion

被引:35
作者
Lee, C [1 ]
Winston, T [1 ]
Unni, A [1 ]
Pagni, RM [1 ]
Mamantov, G [1 ]
机构
[1] UNIV TENNESSEE,DEPT CHEM,KNOXVILLE,TN 37996
关键词
D O I
10.1021/ja953337n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photolysis of 9-methylanthracene (2a; 9-CH(3)An) in a deoxygenated molten salt consisting of 1-ethyl-3-methylimidazolium chloride (1; EMIC) (55 mol %) and AlCl3 at room temperature yielded, in addition to the anti 4 + 4 dimer (3), six products, four of which are dimeric (two oxidized [8 and 9]; two neutral [4 and 5]) and two of which are monomeric (one reduced [7]; one neutral [6]). The same products were produced in CH3CN containing 1. These six products arose by initial electron transfer from 9-MeAn*(1) to EMI(+) to form the radical cation of 9-MeAn and EMI(.). The reduced product 7 arose by electron transfer from EMI(.) to 9-MeAn. This system thus contained both the radical cation and radical anion of 9-MeAn at different stages of the reaction. Experiments using 9-CD(3)An, 2-deuterioEMIC, and 2,4,5-trideuterioEMIC in the molten salt and 9-CH(3)An in the presence of N-1-butylpyridinium chloride (BPC) (BPC/CH3CN) and the molten salt BPC [55 mol %]/AlCl3 clarified mechanistic details.
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页码:4919 / 4924
页数:6
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