Diels-Alder-adducts of dichloromethylenepropanedinitrile; Reactions with nucleophiles

Authors
Friedrich, K Bechtold, K Willin, L Fritz, H
Citation
K. Friedrich et al., Diels-Alder-adducts of dichloromethylenepropanedinitrile; Reactions with nucleophiles, J PRAK CHEM, 342(8), 2000, pp. 819-824
Citations number
7
Categorie Soggetti
Chemistry
Journal title
JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY
ISSN journal
14369966 → ACNP
Volume
342
Issue
8
Year of publication
2000
Pages
819 - 824
Database
ISI
SICI code
1436-9966(2000)342:8<819:DODRWN>2.0.ZU;2-O
Abstract
Upon treatment with aqueous alkali. the Diels-Alder adducts 2 and 4 of dich loromethylenepropane-dinitrile (1) with cyclopentadiene and anthracene resp . are converted into 3-chloro-bicyclo[2.2.1]hepta-2,5-diene-2-carbonitrile (3) and 12-chloro-9,10-dihydro-ethenoanthracene-11-carbonitrile (5). resp. The reaction may be brought about by other nucleophiles as well and involve s the fragmentation of an intermediate beta -chloroimidate anion. 3 is a ed uct for substituted norbornenes such as cyanoketone 18.