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Serendipitous Synthesis of ( tert-Butyl- NNO-azoxy)acetonitrile: Reduction of an Oxime Moiety to a Methylene Unit.
- Source :
-
European Journal of Organic Chemistry . Aug2016, Vol. 2016 Issue 22, p3845-3855. 11p. - Publication Year :
- 2016
-
Abstract
- ( tert-Butyl- NNO-azoxy)acetonitrile ( 1) is a useful precursor for a number of nitrogen heterocycles. It was found that it could be obtained in good yield by treatment of the salts of ( tert-butyl- NNO-azoxy)(hydroxyimino)acetonitrile with NH2OTs. It is the first case of one-step reduction of an oxime group to a methylene unit using an aminating agent. A plausible reaction mechanism is proposed. In addition, a new strategy for the tetrazole 1-oxide ring construction was developed. This involves a diazo-group transfer to the active-methylene unit of compound 1, followed by intramolecular coupling of the azoxy and diazo groups. The tetrazole structures were confirmed by X-ray diffraction analysis. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2016
- Issue :
- 22
- Database :
- Academic Search Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 117296900
- Full Text :
- https://doi.org/10.1002/ejoc.201600584