The Journal of Organic Chemistry

Substitution reactions which proceed via radical-anion intermediates. 31. Electron-transfer substitution reactions: stereochemistry

N Kornblum, PA Wade

Index: Kornblum, Nathan; Wade, Peter A. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 24  p. 5301 - 5305

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Citation Number: 10

Abstract

Substitution of the aliphatic nitro group of optically active 2-(p-nitrophenyl)-2-nitrobutane (11) by sodium azide, sodium thiophenoxide, sodium benzenesulfinate, and the lithium salt of 2- nitropropane invariably occurs with complete loss of optical activity. Furthermore, levorotatory I1 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 ...