Substituent directive effects in 1,2-benzodiazepine synthesis via electrocyclic aromatic substitution by the diazo-group: a rearrangement of 9- to 7-substituted 3H-1,2-benzodiazepines |
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Authors: | Thomas K. Miller John T. Sharp H. Raj Sood Edward Stefaniuk |
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Affiliation: | Department of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ UK |
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Abstract: | The directive effect of aryl-substituents on the site of ring closure in the electrocyclisation of 1-aryl-3-diazoalkenes has been investigated. At 80°C the product ratio is determined by kinetic control but for some substituents the kinetically favoured 9-substituted 3-1,2-benzodiazepines undergo a new rearrangement to their more stable 7-substituted isomers. |
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