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Photoinduzierte Cycloadditionen von 3-Benzyl-2H-azirin


Orahovats, Alexander S; Jackson, Barry; Heimgartner, Heinz; Schmid, Hans (1973). Photoinduzierte Cycloadditionen von 3-Benzyl-2H-azirin. Helvetica Chimica Acta, 56(6):2007-2011.

Abstract

Irradiation of 2-azido-3-phenyl-propene (5) in pentane or benzene solution with a high pressure lamp (Pyrex filter) yields 3-benzyl-2H-azirin (6), which on further irradiation behind quartz or vycor in the presence of trifluoroacetic acid methyl ester or carbon dioxide yields 4-benzyl-5-methoxy-5-trifluoromethyl-3-oxazoline (8) and 4-benzyl-3-oxazolin-5-one (9), respectively (scheme 2). A small amount of 3-phenylacetonitrile is also formed.

Abstract

Irradiation of 2-azido-3-phenyl-propene (5) in pentane or benzene solution with a high pressure lamp (Pyrex filter) yields 3-benzyl-2H-azirin (6), which on further irradiation behind quartz or vycor in the presence of trifluoroacetic acid methyl ester or carbon dioxide yields 4-benzyl-5-methoxy-5-trifluoromethyl-3-oxazoline (8) and 4-benzyl-3-oxazolin-5-one (9), respectively (scheme 2). A small amount of 3-phenylacetonitrile is also formed.

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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:1973
Deposited On:09 Dec 2014 15:40
Last Modified:08 Dec 2017 08:44
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19730560621

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