Journal of Organic Chemistry p. 5301 - 5305 (1987)
Update date:2022-08-03
Topics: Electrophilic Aromatic Substitution (EAS) SN1 Reaction
Kornblum, Nathan
Wade, Peter A.
Substitution of the aliphatic nitro group of optically active 2-(p-nitrophenyl)-2-nitrobutane (II) by sodium azide, sodium thiophenoxide, sodium benzenesulfinate, and the lithium salt of 2-nitropropane invariably occurs with complete loss of optical activity.Furthermore, levorotatory II is racemized by sodium nitrite.These facts support the view that substitution reactions in p-nitrocumyl systems proceed via the electron-transfer chain mechanism of eq 2-5.
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