Regioselectivity of photochemical and thermal Smiles rearrangements and related reactions of. beta.-(nitrophenoxy) methylamines

GG Wubbels, AM Halverson, JD Oxman…

Index: Wubbels, Gene G.; Halverson, Ann M.; Oxman, Joe D. Journal of the American Chemical Society, 1980 , vol. 102, # 14 p. 4848 - 4849

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Citation Number: 31

Abstract

Results Two methods were developed for synthesizing/3-(nitrophenoxy) ethylamines (1-3) as hydrochlorides. The first, outlined in Scheme I, uses 2-chloroethanol to alkylate a nitrophenol; the hydroxyl group of the produd is activated by conversion to a tosylate, and