Photochemical reactions. Part 20. Photolysis of o-nitrobenzaldehyde N-acylhydrazones leading to benzyne and 5-nitrophthalazines
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 553-557
- https://doi.org/10.1039/p19790000553
Abstract
Irradiation of o-nitrobenzaldehyde N-acetyl-N-alkylhydrazones resulted in the generation of benzyne via decomposition of o-(N-acetyl-N-alkyltriazeno)benzoic acids derived from o-nitrosobenzoyl-N-acetyl-N-alkylhydrazides which are initially formed in an analogous fashion to the o-nitrobenzylideneaniline rearrangement. Photolysis of o-nitrobenzaldehyde N-acylhydrazones, however, resulted in photocyclisation leading to 1-substituted 5-nitrophthalazines, with benzyne generation only as a minor process.Keywords
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