Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds
| Autor: | Dmitrij V Semenok, Jury J. Medvedev, Valerij A. Nikolaev, Liudmila L. Rodina, Xenia V. Azarova |
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| Rok vydání: | 2018 |
| Předmět: |
C–H insertion
diazo compounds chemistry.chemical_element Hydrazone 010402 general chemistry 01 natural sciences Medicinal chemistry Full Research Paper lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry excited state lcsh:Science Wolff rearrangement Alkyl chemistry.chemical_classification photochemistry 010405 organic chemistry Chemistry Organic Chemistry Photodissociation Nitrogen 0104 chemical sciences Photoexcitation Yield (chemistry) lcsh:Q Diazo |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 2250-2258 (2018) |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.14.200 |
| Popis: | The sensitized photoexcitation of 2-diazocyclopentane-1,3-diones in the presence of THF leads to the insertion of the terminal N-atom of the diazo group into the α-С–Н bond of THF, producing the associated N-alkylhydrazones in yields of up to 63–71%. Further irradiation of hydrazones derived from furan-fused tricyclic diazocyclopentanediones culminates in the cycloelimination of furans to yield 2-N-(alkyl)hydrazone of cyclopentene-1,2,3-trione. By contrast, the direct photolysis of carbocyclic diazodiketones gives only Wolff rearrangement products with up to 90–97% yield. |
| Databáze: | OpenAIRE |
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