Studies of tertiary amine oxides. 9. Thermal rearrangement of 1-(4-substituted) phenylpiperidine N-oxides to the corresponding N-hydroxylamines

AH Khuthier, KY Al-Mallah, SY Hanna…

Index: Khuthier, Abdul-Hussain; Al-Mallah, Khawla Y.; Hanna, Salim Y.; Abdulla, Noor-Aldeen I. Journal of Organic Chemistry, 1987 , vol. 52, # 9 p. 1710 - 1713

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Citation Number: 20

Abstract

(4-Substituted-pheny1) piperidine N-oxides undergo a thermal rearrangement to 0- arylhydroxylamines. Electron-withdrawing substituents are essential for the rearrangement and must be ortho or para relative to the 3N-O function. The reaction has been found to be first order in substrate when rates were measured in dioxane, and the activation parameters were calculated. The order of reactivity in this rearrangement is NO2>> CN> COPh> ...

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