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Inter- und intramolekulare Abfangreaktionen photochemisch erzeugter Diarylnitrilimine


Meier, Hansruedi; Heinzelmann, Willy; Heimgartner, Heinz (1980). Inter- und intramolekulare Abfangreaktionen photochemisch erzeugter Diarylnitrilimine. CHIMIA International Journal for Chemistry, 34(12):506-508.

Abstract

Inter- and intramolecular trapping reactions of photochemically generated diarylnitrilimines
Photolysis of 2,5-diphenyltetrazole (2a) in an ether/pentane/ethanol glass at 77 K in the presence of a 10fold excess of propionic acid yields diphenylnitrilimine (1b). Warming up the solution to 130 K 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 135 K 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.

Abstract

Inter- and intramolecular trapping reactions of photochemically generated diarylnitrilimines
Photolysis of 2,5-diphenyltetrazole (2a) in an ether/pentane/ethanol glass at 77 K in the presence of a 10fold excess of propionic acid yields diphenylnitrilimine (1b). Warming up the solution to 130 K 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 135 K 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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1980
Deposited On:29 Jul 2014 11:06
Last Modified:08 Dec 2017 06:39
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Swiss National Science Foundation
Official URL:https://chimia.ch/index.php?lang=en

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