Electrochemically induced aromatic substitution. The 2-nitropropane anion, a powerful nucleophile in SRN1 aromatic substitution

C Amatore, M Gareil, MA Oturan, J Pinson…

Index: Amatore, Christian; Gareil, Monique; Oturan, Mehmet A.; Pinson, Jean; Saveant, Jean-Michel; Thiebault, Andre Journal of Organic Chemistry, 1986 , vol. 51, # 20 p. 3757 - 3761

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Citation Number: 23

Abstract

In contrast with previous reports, the 2-nitropropane anion reacts readily with aryl radicals in the context of aromatic Sml processes. This is shown in the examples of 4- bromobenzophenone and iodobenzene under electrochemical stimulation. The substitution products do not, however, result from the simple addition of the 2-nitropropyl anion on the aryl radical. The ensuing anion radical is indeed unstable, cleaving off a nitrite ion and ...