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Heterocyclole als Zwischenprodukte einer neuen, überraschenden Umlagerung bei der Reaktion von 3-(Dimethylamino)-2,2-dimethyl-2H-azirin mit monosubstituierten Parabansäuren


Dähler, Marlise; Prewo, Roland; Bieri, Jost H; Heimgartner, Heinz (1983). Heterocyclole als Zwischenprodukte einer neuen, überraschenden Umlagerung bei der Reaktion von 3-(Dimethylamino)-2,2-dimethyl-2H-azirin mit monosubstituierten Parabansäuren. Helvetica Chimica Acta, 66:1456-1465.

Abstract

Cyclols as Intermediates in the Reaction of 3-(Dimethylamino)-2,2-dimethyl-2H-azirine with Monosubstituted Parabanic Acids; a New and Unexpected Rearrangement. The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) with N-methyl- parabanic acid (4) in 2-propanol at room temperature gives the cyclol 5 in 97% yield. In acetonitrile solution 5 rearranges to the imidazoline derivative 6 (Scheme 2). The structures of the unexpected products 5 and 6 have been established by X-ray crystallography.

Abstract

Cyclols as Intermediates in the Reaction of 3-(Dimethylamino)-2,2-dimethyl-2H-azirine with Monosubstituted Parabanic Acids; a New and Unexpected Rearrangement. The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) with N-methyl- parabanic acid (4) in 2-propanol at room temperature gives the cyclol 5 in 97% yield. In acetonitrile solution 5 rearranges to the imidazoline derivative 6 (Scheme 2). The structures of the unexpected products 5 and 6 have been established by X-ray crystallography.

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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:1983
Deposited On:08 Jul 2014 10:45
Last Modified:18 Apr 2018 11:45
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel
OA Status:Closed
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSchweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche & Co. AG, Basel

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