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Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit Benzoyl-, Äthoxycarbonyl- und Vinylphosphonaten


Gakis, Nikolas; Heimgartner, Heinz; Schmid, Hans (1975). Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit Benzoyl-, Äthoxycarbonyl- und Vinylphosphonaten. Helvetica Chimica Acta, 58(3):748-760.

Abstract

The irradiation of the 3-phenyl-2H-azirines 1a-c in the presence of diethyl benzoylphosphonate (8) in cyclohexane solution, using a mercury high pressure lamp (pyrex filter), yields the diethyl (4,5-diphenyl-3-oxazolin-5-yl)-phosponates 9a-c (Scheme 3). In the case of 1b a mixture of two diastereomeric 3-oxazolines, resulting from a regiospecific but non-stereospecific cycloaddition of the benzonitrile-benzylide dipole 2b to the carbonyl group of the phosphonate 8, was isolated. Benzonitrile-isopropyIide (2a), generated from 2,2-dimethyl-3-phenyl-2H-azirine (1a), undergoes a cycloaddition reaction to the ester-carbonyl group of diethyl ethoxycarbonyl-phosphonate (15) with the same regiospecificity to give the 3-oxazoline derivative 16 (Scheme 5). The azirines 1a-c, on irradiation in benzene in the presence of diethyl vinylphosphonate (17) give non-regiospecifically the delta1-pyrrolines 13a-c and 14a-c (Scheme 6).

Abstract

The irradiation of the 3-phenyl-2H-azirines 1a-c in the presence of diethyl benzoylphosphonate (8) in cyclohexane solution, using a mercury high pressure lamp (pyrex filter), yields the diethyl (4,5-diphenyl-3-oxazolin-5-yl)-phosponates 9a-c (Scheme 3). In the case of 1b a mixture of two diastereomeric 3-oxazolines, resulting from a regiospecific but non-stereospecific cycloaddition of the benzonitrile-benzylide dipole 2b to the carbonyl group of the phosphonate 8, was isolated. Benzonitrile-isopropyIide (2a), generated from 2,2-dimethyl-3-phenyl-2H-azirine (1a), undergoes a cycloaddition reaction to the ester-carbonyl group of diethyl ethoxycarbonyl-phosphonate (15) with the same regiospecificity to give the 3-oxazoline derivative 16 (Scheme 5). The azirines 1a-c, on irradiation in benzene in the presence of diethyl vinylphosphonate (17) give non-regiospecifically the delta1-pyrrolines 13a-c and 14a-c (Scheme 6).

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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:1975
Deposited On:18 Nov 2014 15:12
Last Modified:08 Dec 2017 08:11
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19750580311

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