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Abstract

The subject invention relates to a method of synthesizing nitroxides from secondary amines. This method uses a suitable dioxirane compound such as dimethyldioxirane (DMD), which is relatively stable and simple to synthesize, as the oxidizing agent. A quantity of a secondary amine having no hydrogen atoms directly attached to the alpha carbon atoms is mixed with a 2x molar ratio of the dioxirane. In a first reaction, the secondary amine is oxidized to form a hydroxylamine; in a second reaction, the hydroxylamine is further oxidized to form a nitroxide. When the dioxirane loses an oxygen atom it converts into a ketone; for example, dimethyldioxirane is converted into acetone. This is very convenient, since the ketone byproduct is a solvent that can be easily removed after the reaction without causing interfering reactions. This method provides a simple, highly selective, rapid reaction with very high yields. It can be carried out in a single reaction vessel and can be used with a wide variety of secondary amines (including secondary amines having more than one amine group) to create a corresponding variety of nitroxides.

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Patent Number

US5087752A

Assignee

University of Missouri System

Application Number

US07581520

Date Filed

9-12-1990

Issue Date

2-11-1992

Synthesis of nitroxides using dioxiranes

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