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Review | Regular issue | Vol 2, No. 6, 1974, pp.669-743
Published online, 1st January, 1970
DOI: 10.3987/R-1974-06-0669
Cyclic Hydroxylamines; A Review of Preparative Methods and Properties

Ronald T. Coutts* and Abdel-monaem M. K. El-hawari

*Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada


The preparation of cyclic hydroxylamines by various methods is discussed. These methods include (a) direct N-oxidation of amines, (b) reduction of cyclic nitrones, (c) addition to cyclic nitrones, (d) reductive and non-reductive cyclization reactions, as well as other miscellaneous methods.
The physical and chemical properties of cyclic hydroxylamines which are also discussed are (a) solubility and salt formation, (b) qualitative and quantitative analysis, (c) molecular spectroscopy and mass spectrometry, (d) stability, (e) tautomerism, (f) oxidation, (g) reduction, (h) alkylation reactions, (i) acylation and sulfonation reactions, (j) reactions with nucleophilic reagents, and (k) reactions with electrophilic reagents. Some comments on the biological importance of cyclic hydroxylamines and related compounds are included in an introductory section.