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Bildung eines Azacyclols durch transanulare Ringkontraktion


Schläpfer-Dähler, Marlise; Prewo, Roland; Bieri, Jost H; Germain, Gabriel; Heimgartner, Heinz (1988). Bildung eines Azacyclols durch transanulare Ringkontraktion. CHIMIA International Journal for Chemistry, 42(1):25-26.

Abstract

Reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with phthalimide (8) in polar solvents yields the (1:1)-adduct 2-dimethylamino-9b-hydroxy-3,3-dimethyl-5,9b-dihydro-3H-imidazo[2,1a]isoindol-5-one (10). The structure of this azacyclol has been established by X-ray crystallography. A reaction mechanism via ring expansion to an eight-membered heterocycle followed by transannular ring contraction explains the formation of 10.

Abstract

Reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with phthalimide (8) in polar solvents yields the (1:1)-adduct 2-dimethylamino-9b-hydroxy-3,3-dimethyl-5,9b-dihydro-3H-imidazo[2,1a]isoindol-5-one (10). The structure of this azacyclol has been established by X-ray crystallography. A reaction mechanism via ring expansion to an eight-membered heterocycle followed by transannular ring contraction explains the formation of 10.

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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:1988
Deposited On:14 May 2014 08:58
Last Modified:08 Dec 2017 05:19
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel
Related URLs:http://www.ingentaconnect.com/content/00094293/

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