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

✍ Scribed by Miguel E. Alonso; Sarah V. Pekerar; Maria L. Borgo


Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
664 KB
Volume
28
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

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 ^13^C NMR. Appropriate ^1^H 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 ^13^C 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.


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