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

…, AM Halverson, JD Oxman, VH De Bruyn

Index: Wubbels, Gene G.; Halverson, Ann M.; Oxman, Joe D.; Bruyn, Van H. De Journal of Organic Chemistry, 1985 , vol. 50, # 23 p. 4499 - 4504

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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 replaced by phthalimide. Hydrolysis of the phthalimide is best done in acid; use of hydrazine to cleave the ortho and para precursors of 1 and 3 results in some attack on the ...