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Photoinduzierte 1,3-dipolare Cycloaddition von 3-Phenyl-2H-azirinen an Azodicarbonsäure-diäthylester


Gilgen, Paul; Heimgartner, Heinz; Schmid, Hans (1974). Photoinduzierte 1,3-dipolare Cycloaddition von 3-Phenyl-2H-azirinen an Azodicarbonsäure-diäthylester. Helvetica Chimica Acta, 57(5):1382-1392.

Abstract

Irradiation of 2,2-dimethyl-3-phenyl- (1a), 2,3-diphenyl-2H-azirine (1b) or the azirine-precursors 1-azido-1-phenyl-propene (2a) and 1-azido-1-phenyl-ethylene (2b), respectively, in benzene in the presence of azodicarboxylic acid diethylestcr, yields the corresponding 1,2-carbethoxy-3-phenyl-delta3-1,2,4-triazolines 4a-d (Scheme 1).
Refluxing 4 (a, c or d) in 0.2-0.4M aqueous ethanolic potassium hydroxide leads to the formation of the 1-carbethoxy-3-phenyl-delta2-1,2,4-triazolines 6 (a,c or d). Under the same conditions 4b is converted to 3,5-diphenyl-1,2,4-triazole (7b, Scheme 2). In 10M aqueous potassium hydroxide solution heating of either 4 (c or d) or 6 (c or d) yields the 3-phenyl-1,2,4-triazoles 7 (c or d).
Photolysis of 1-carbethoxy-5,5-dimethyl-3-phenyl-delta2-1,2,4-triazoline (6a) in benzene in the presence of oxygen and trifluoroacetic acid methylester gives the 5-methoxy-2,2-dimethyl-4-phenyl-5-trifluoromethyl-3-oxazoline (13, Scheme 5). 5,5-Dimethyl-3-phenyl-1,2,4-triazole seems to be the intermediate, which on losing nitrogen gives the benzonitrile-isopropylide (3a).

Abstract

Irradiation of 2,2-dimethyl-3-phenyl- (1a), 2,3-diphenyl-2H-azirine (1b) or the azirine-precursors 1-azido-1-phenyl-propene (2a) and 1-azido-1-phenyl-ethylene (2b), respectively, in benzene in the presence of azodicarboxylic acid diethylestcr, yields the corresponding 1,2-carbethoxy-3-phenyl-delta3-1,2,4-triazolines 4a-d (Scheme 1).
Refluxing 4 (a, c or d) in 0.2-0.4M aqueous ethanolic potassium hydroxide leads to the formation of the 1-carbethoxy-3-phenyl-delta2-1,2,4-triazolines 6 (a,c or d). Under the same conditions 4b is converted to 3,5-diphenyl-1,2,4-triazole (7b, Scheme 2). In 10M aqueous potassium hydroxide solution heating of either 4 (c or d) or 6 (c or d) yields the 3-phenyl-1,2,4-triazoles 7 (c or d).
Photolysis of 1-carbethoxy-5,5-dimethyl-3-phenyl-delta2-1,2,4-triazoline (6a) in benzene in the presence of oxygen and trifluoroacetic acid methylester gives the 5-methoxy-2,2-dimethyl-4-phenyl-5-trifluoromethyl-3-oxazoline (13, Scheme 5). 5,5-Dimethyl-3-phenyl-1,2,4-triazole seems to be the intermediate, which on losing nitrogen gives the benzonitrile-isopropylide (3a).

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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:1974
Deposited On:01 Dec 2014 16:19
Last Modified:05 Apr 2016 18:34
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung

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