Synthesis of nitroxides using dioxiranes
US5087752A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 12, 1990 |
| Grant date | Feb 11, 1992 |
| Priority date | — |
| Expiry date | Sep 12, 2010 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C291/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.