Reaction of benzofurazan N-oxide with secondary aliphatic amines; preparation of NN-dialkyl-N′-(o-nitrophenyl)hydrazines
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 20,p. 2216-2221
- https://doi.org/10.1039/p19760002216
Abstract
The interaction of benzofurazan N-oxide with a variety of secondary aliphatic amines in the cold gives NN-dialkyl-N′-(o-nitrophenyl)hydrazines by attack on the hetero-ring. At higher temperatures, dialkylaminobenzofurazans are obtained by attack on the benzene ring. Substituents in the benzofuran N-oxide exerting –I and –M effects slow down both processes. The interaction of various NN-dialkylhydrazines with chloronitrobenzenes and polynitrobenzenes give either nitrophenyldialkyl-amines or -hydrazines in a predictable manner, for which a mechanistic rationale is proposed, involving charge-transfer complex formation when polynitrobenzenes are used.Keywords
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