Synthesis of hydroxylamines using dioxiranes

Details Synthesis of hydroxylamines using dioxiranes Synthesis of hydroxylamines using dioxiranes

1989-09-14

1991-03-19

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548216, 548565, 546290, 564300, 564301, C07B 4100, C07C23900, C07D32100, C07J 4300

Patent

active

050012339

ABSTRACT:
The subject invention relates to a method of synthesizing hydroxylamines from secondary amines. This method uses a dioxirane compound such as dimethyldioxirane (DMD, which is relatively stable and simple to synthesize), as the oxidizing agent. The reaction proceeds as follows: ##STR1## This method provides a simple, one-step reaction with high yields. It can be performed in acetone solution, and the transferral of an oxygen atom from dimethyldioxirane to the secondary amine converts the dioxirane into acetone, the solvent, permitting simple workup and purification. This method can be used with a wide variety of secondary amines, including aliphatic, aromatic, cyclic, and heterocyclic secondary amines, to create a corresponding variety of hydroxylamines.

REFERENCES:
Murray, Robert W. et al, "Dioxiranes: Synthesis and Reactions of Methyldioxiranes", The Journal of Organic Chemistry 50: 2847-2853 (1985).
Jean Jacques Yaouanc, et al, "Nucleophilic Oxidation with Bis Diphenylphosphinyl Peroxide: Direct Preparation of O-Phosphinylated Aminating Reagents", Synthesis 1985: 807 (Aug. 1985).
Murray, Robert W. et al, "A New Synthesis of Nitro Compounds Using Dimethyldioxirane", Tetrahedron Letters 27 (21): 2335-2336 (1986).
Murray, Robert W. and Singh, Megh, "A Convenient High Yield Synthesis of Nitroxides", Tetrahedron Letters 29 (37): 4677-4680 (Oct. 1988).
Zajec et al "Oxidation of Amines . . . ", J. Am. Chem. Soc. 53 (25) 5856-5860 (1988).

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