Transmission of electronic effects through 2-[donor]-1-[acceptor]-cyclopropane

The through‐ring conjugation between π‐donor and attractor substitutents on vicinal carbons of cyclopropane with the direct participation of the ring was assessed using proton and 13C NMR. Appropriate 1H NMR correlations were obtained between σp and δH of the trimethylene protons. However, aryl thro...

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Veröffentlicht in:Magnetic resonance in chemistry 1990-11, Vol.28 (11), p.956-962
Hauptverfasser: Alonso, Miguel E., Pekerar, Sarah V., Borgo, Maria L.
Format: Artikel
Sprache:eng
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Zusammenfassung:The through‐ring conjugation between π‐donor and attractor substitutents on vicinal carbons of cyclopropane with the direct participation of the ring was assessed using proton and 13C NMR. Appropriate 1H NMR correlations were obtained between σp and δH of the trimethylene protons. However, aryl through‐space field effects were found to obscure individual conjugative effects. Conversely, the 13C NMR data implied the occurrence of competitive conjugation of π‐groups with the ring but gave no proof for the existence of the actual transmission of conjugative effects through the C‐1–C‐2 bond of the ring.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.1260281110