Header

UZH-Logo

Maintenance Infos

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.

Statistics

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:05 Apr 2016 17:49
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/

Download

Full text not available from this repository.

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations