期刊
CANADIAN JOURNAL OF CHEMISTRY
卷 81, 期 10, 页码 1108-1118出版社
CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS
DOI: 10.1139/V03-149
关键词
1-methyl-5-nitroindole; 5-nitrobenzofurane; 5-nitrobenzothiophene; iminoquinone; electrosynthesis
Preparative electrolysis of 1-methyl-5-nitroindole (1b, X = NCH3), 5-nitrobenzofurane (1c, X = O), and 5-nitrobenzothiophene (1d, X = S) at Hg, in acidic hydromethanolic media, leads to the formation of the corresponding 4-substituted amino derivatives 5, which result from the 100% regioselective addition to iminoquinone-type intermediate 4 of methanol or of any other good nucleophile present in the electrolytic solution. In acidic medium, the iminoquinonium intermediates 4b and 4c were trapped in a cycloaddition reaction with cyclopentadiene added to the electrolysis medium. The regiochemistry of the nucleophilic addition is discussed in light of AM1 calculations.
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