Header

UZH-Logo

Maintenance Infos

Selenium-containing heterocycles from isoselenocyanates: Base-catalyzed reaction of malononitrile with phenyl isoselenocyanate and bromoacetonitrile or alpha-halogenated ketones


Sommen, G L; Linden, A; Heimgartner, H (2007). Selenium-containing heterocycles from isoselenocyanates: Base-catalyzed reaction of malononitrile with phenyl isoselenocyanate and bromoacetonitrile or alpha-halogenated ketones. Helvetica Chimica Acta, 90(10):1849-1855.

Abstract

The reaction of phenyl isoselenocyanate (1a) with malononitrile (= propanedinitrile) in DMF in the presence of Et3N leads to the intermediate ketene N,Se-hemiacetal 6a, which can be trapped with bromoacetonitrile or a-halogenated ketones 12a and 12b (Scheme 3). The products are [(alkylseleno)-(phenylamino)methylene]malononitriles 10 and 13, which are obtained in good yield. In the case of the (2-oxoalkyl)seleno derivatives 13, they are in equilibrium with the cyclic hemiacetals 14. Chemical and spectroscopic evidence for the structures of the new compounds are described. The structure of 14a was
established by X-ray crystallography.

Abstract

The reaction of phenyl isoselenocyanate (1a) with malononitrile (= propanedinitrile) in DMF in the presence of Et3N leads to the intermediate ketene N,Se-hemiacetal 6a, which can be trapped with bromoacetonitrile or a-halogenated ketones 12a and 12b (Scheme 3). The products are [(alkylseleno)-(phenylamino)methylene]malononitriles 10 and 13, which are obtained in good yield. In the case of the (2-oxoalkyl)seleno derivatives 13, they are in equilibrium with the cyclic hemiacetals 14. Chemical and spectroscopic evidence for the structures of the new compounds are described. The structure of 14a was
established by X-ray crystallography.

Statistics

Citations

7 citations in Web of Science®
7 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

259 downloads since deposited on 20 Oct 2011
13 downloads since 12 months
Detailed 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:English
Date:2007
Deposited On:20 Oct 2011 12:37
Last Modified:07 Dec 2017 09:14
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Dr. Helmut Legerlotz-Foundation, Univeristät Zürich, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200790194

Download