The Journal of Organic Chemistry

Further evidence for nitrenium ion intermediacy in N-phenylhydroxylamine rearrangement to aminophenol

LA Sternson, R Chandrasakar

Index: Sternson, L. A.; Chandrasakar, R. Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4295 - 4297

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Citation Number: 9

Abstract

Pressure Reactions. A solution of triphenylphosphine (0.25 mmol), alkyl halide or sulfonate (0.50 mmol), and solvent (0.8 mL, acetonitrile or benzene: toluene, 7: 3 mole ratio) in a Teflon tube clamped at both ends was pressurized at 15 kbar (1.5 GPa) hydrostatic pressure for 24-36 h at 20-40" C (see Tables I and I1 for solvent and exact conditions). The reactions were cooled (if necessary), depressurized, and concentrated under reduced pressure to ...