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1,3-Dipolare Cycloadditionen von Nitrilium-Betainen mit 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thion


Büchel, Thomas; Prewo, Roland; Bieri, Jost H; Heimgartner, Heinz (1984). 1,3-Dipolare Cycloadditionen von Nitrilium-Betainen mit 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thion. Helvetica Chimica Acta, 67:534-549.

Abstract

1,3-Dipolar Cycloadditions of Nitrilium Betaines with 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thione
Benzonitrile ylides, imines, and oxides undergo smooth 1.3-dipolar cycloaddition reactions with the exocyclic C,S-double bond of 4,4-dimethyli-2-phenyl-2-thiazolin-5- thione (1), yielding heterocyclic spiro-compounds. The structure of the cycloadducts 5c, 5c', and 3f (Fig.) have been established by X-ray structure analysis.
With the benzonitrile ylides, the two regioisomeric cycloaddition modes have been observed, depending on the substituents of the ylide-C-atom. It is questionable, whether the reaction of 1 and the oxazaphosphol 8 (Schemes 8 and 13) proceeds via the corresponding nitrile ylide as an intermediate.

Abstract

1,3-Dipolar Cycloadditions of Nitrilium Betaines with 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thione
Benzonitrile ylides, imines, and oxides undergo smooth 1.3-dipolar cycloaddition reactions with the exocyclic C,S-double bond of 4,4-dimethyli-2-phenyl-2-thiazolin-5- thione (1), yielding heterocyclic spiro-compounds. The structure of the cycloadducts 5c, 5c', and 3f (Fig.) have been established by X-ray structure analysis.
With the benzonitrile ylides, the two regioisomeric cycloaddition modes have been observed, depending on the substituents of the ylide-C-atom. It is questionable, whether the reaction of 1 and the oxazaphosphol 8 (Schemes 8 and 13) proceeds via the corresponding nitrile ylide as an intermediate.

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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
Scopus Subject Areas:Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Language:German
Date:1984
Deposited On:25 Jun 2014 14:10
Last Modified:30 Jul 2020 13:53
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel, Dr. J. Hoop-Stiftung, Ivoclar AG, Schaan FL
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/hlca.19840670222
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSchweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche & Co. AG, Basel
  • : Funder
  • : Grant ID
  • : Project TitleDr. J. Hoop-Stiftung, Ivoclar AG, Schaan FL

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