The Journal of Organic Chemistry

Oxidative aromatic nitration with charge-transfer complexes of arenes and nitrosonium salts

EK Kim, JK Kochi

Index: Kim, E. K.; Kochi, J. K. Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1692 - 1702

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Citation Number: 45

Abstract

Brightly colored solutions are obtained immediately upon the exposure of various arenes (ArH) to nitrosonium (NO+) salts. The colors arise from the charge-transfer transitions of 1: l complexes [ArH, NO+] that are reversibly formed as persistent intermediates. However the yellow-red charge-transfer (CT) colors are readily bleached by dioxygen, and the corresponding nitroarenes (ArN02) can be isolated in excellent yields from acetonitrile ...