1,3-dipolar cycloadditions of aromatic azoxy compounds to strained cyclo-alkenes |
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Authors: | Rolf Huisgen Francisco Palacios Gambra |
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Institution: | Institut für Organische Chemie der Universität München Karlstr. 23, 8000 München 2, Germany |
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Abstract: | The 1,2,3-oxadiazolidines resulting from the addition of 4,4′-dicyano-azoxybenzene to trans-cyclooctene or cis, trans-cycloocta-1,5-diene are not stable, bu suffer 1,3-dipolar cycloreversion to give an azomethine imine; this intermediate is either captured by a second molecule of the strained cycloalkene to give 1:2 adducts in high yields or it tautomerizes to an enehydrazine. 4,4′-Dinitroazoxybenzene and benzoc]cinnoline N-oxide react analogously. |
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