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Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit Aldehyden


Giezendanner, Heinz; Heimgartner, Heinz; Jackson, Barry; Winkler, Tammo; Hansen, Hans-Jürgen; Schmid, Hans (1973). Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit Aldehyden. Helvetica Chimica Acta, 56(7):2611-2627.

Abstract

Experiments concerning the photochemical condensation of 3-phenyl-2H-azirines 1 with aliphatic and aromatic aldehydes to 3-oxazolines 4 are fully described (cf. scheme 1). Photochemically nitrile methylides of type 2 are first formed, which then very quickly react thermally with the aldehydes in a regiospecific manner to give the 3-oxazolines 4. Azirines monosubstituted in position 2 (1b and 1c) give mixtures of cis,trans-oxazoline isomers, in which the cis isomer predominates. The stereoselectivity of the cycloaddition reaction can be rationalized by a simple model (scheme 10). The stereoisomeric 3-oxazolines 4 are distinguishable in the NMR spectra by the large homoallylic coupling constants between the H atoms on C(2) and C(5).

Abstract

Experiments concerning the photochemical condensation of 3-phenyl-2H-azirines 1 with aliphatic and aromatic aldehydes to 3-oxazolines 4 are fully described (cf. scheme 1). Photochemically nitrile methylides of type 2 are first formed, which then very quickly react thermally with the aldehydes in a regiospecific manner to give the 3-oxazolines 4. Azirines monosubstituted in position 2 (1b and 1c) give mixtures of cis,trans-oxazoline isomers, in which the cis isomer predominates. The stereoselectivity of the cycloaddition reaction can be rationalized by a simple model (scheme 10). The stereoisomeric 3-oxazolines 4 are distinguishable in the NMR spectra by the large homoallylic coupling constants between the H atoms on C(2) and C(5).

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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 15:38
Last Modified:05 Apr 2016 18:35
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19730560745

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