Journal of Organic Chemistry p. 3757 - 3761 (1986)
Update date:2022-08-30
Topics:
Amatore, Christian
Gareil, Monique
Oturan, Mehmet A.
Pinson, Jean
Saveant, Jean-Michel
Thiebault, Andre
In contrast with previous reports, the 2-nitropropane anion reacts readily with aryl radicals in the context of aromatic SRN1 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 thus leading to the cumene derivative as the main substitution product.Comparison of reactivity with diethyl phosphite and thiophenoxide ions shows that the 2- nitropropane anion is a quite powerful nucleophile in aromatic SRN1 reactions.
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