Issue 6, 1991

Efficient direct aromatic amination by parent nitrenium ion. Photolyses of 1-aminopyridinium and 1-aminoquinolinium salts and effect of crown ethers

Abstract

Photolyses of 1-aminopyridinium salts 1af, 2-aminoisoquinolinium salt 2 and 1-aminoquinolinium salts 3af gave aniline 4 or a mixture of 2-, 3- and 4-toluidines 5a7a in benzene–trifluoroacetic acid (TFA) or in toluene–TFA, respectively. The use of 1-aminoquinolinium perchlorate 3a showed the highest yield in these photolyses. Irradiation of 3a in the presence of ethylbenzene, p-xylene, mesitylene, anisole and chlorobenzene similarly yielded arylamines. The yields of arylamines were generally increased in the presence of a small amount of crown ether. The aromatic amination is discussed in terms of the intermediacy of a parent nitrenium ion.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 1525-1529

Efficient direct aromatic amination by parent nitrenium ion. Photolyses of 1-aminopyridinium and 1-aminoquinolinium salts and effect of crown ethers

H. Takeuchi, D. Higuchi and T. Adachi, J. Chem. Soc., Perkin Trans. 1, 1991, 1525 DOI: 10.1039/P19910001525

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