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

Bienfait, B.;Coppemotte, G.;Merenyi, R.;Viehe, HG.;Sustmann, R.;et.al.
(1991) Tetrahedron — Vol. 47, n° 38, p. 8167-8176 (1991)

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Authors
  • Bienfait, B.
    Author
  • Coppemotte, G.
    Author
  • Merenyi, R.
    Author
  • Viehe, HG.
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  • Sustmann, R.
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Abstract
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).
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Bienfait, B., Coppemotte, G., Merenyi, R., Viehe, HG., Sicking, W., & Sustmann, R. (1991). Beta-cyanocyclobutenone As a Highly Reactive Dienophile in Comparison To Beta-cyanocyclopentenone. Tetrahedron, 47(38), 8167-8176. https://doi.org/10.1016/S0040-4020(01)91012-9 (Original work published 1991)