Inter- und intramolekulare Abfangreaktionen photochemisch erzeugter Diarylnitrilimine
Photolysis of 2,5-diphenyltetrazoIe (2a) in an ether/pentane/ ethanol-glass at 77K in the presence of a 10fold excess of propionic acid yields diphenylnitrilimine (1b). Warming up the solution to 130K leads to the formation of the ethanol adduct 5 (scheme 1 and fig. 1). Irradiation of 2a and propio...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1980-12-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9496 |
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| Summary: | Photolysis of 2,5-diphenyltetrazoIe (2a) in an ether/pentane/ ethanol-glass at 77K in the presence of a 10fold excess of propionic acid yields diphenylnitrilimine (1b). Warming up the solution to 130K leads to the formation of the ethanol adduct 5 (scheme 1 and fig. 1). Irradiation of 2a and propionic acid in a hydrocarbon glass at 77 K and raising the temperature to 135K gives the adduct 3, which at 200 K undergoes a rearrangement to the N'-phenyl-N'-propionyl-benzohydrazide (4, scheme 1 and fig. 2). In the case of the tetrazole 6, the primarily formed nitrilimine 7 leads to the heterocyclic system 8 via intramolecular 1,3-dipolar cycloaddition (scheme 2 and fig. 3). The intermediate 7 can be trapped with propionic acid in the photolysis of 6 in a dioxane solution at room temperature.
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| ISSN: | 0009-4293 2673-2424 |