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Beta-cyanocyclobutenone As a Highly Reactive Dienophile in Comparison To Beta-cyanocyclopentenone

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Bienfait, B. Coppemotte, G. Merenyi, R. Viehe, HG. Sicking, W. Sustmann, R.

The thermal [2+2] cycloaddition of alpha-chloroacrylonitrile to allene followed by ozonolysis, then elimination of HCl provides access to the new beta-cyanocyclobutenone 1 (Scheme 1). Diels-Alder reactions of 1 occur very easily at room temperature. The high reactivity of 1 in [4+2] cycloadditions strongly contrasts with the low reactivity of the homologous cyanocyclopentenone 9 (Scheme 4). This is in agreement with calculations (PM3 method).

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 1991
Language Anglais
Journal information "Tetrahedron" - Vol. 47, no. 38, p. 8167-8176 (1991)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4020
e-issn 1464-5416
Publication status Publié
Affiliation UCL
Keywords CYCLOBUTENONE ; CYCLOPENTENONE ; DIELS-ALDER ; TRANSITION STATE ; PM3 CALCULATION
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Bibliographic reference Bienfait, B. ; Coppemotte, G. ; Merenyi, R. ; Viehe, HG. ; Sicking, W. ; et. al. Beta-cyanocyclobutenone As a Highly Reactive Dienophile in Comparison To Beta-cyanocyclopentenone. In: Tetrahedron, Vol. 47, no. 38, p. 8167-8176 (1991)
Permanent URL http://hdl.handle.net/2078.1/50876