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Long range substituent effects relfected in the 13C NMR spectra of allyl alcohols and their derivatives

✍ Scribed by Ernest Wenkert; Miroslav J. Gašić; Edward W. Hagaman; L. D. Kwart

Publisher: John Wiley and Sons
Year: 1975
Tongue: English
Weight: 282 KB
Volume: 7
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270070112

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✦ Synopsis

Abstract

Acylation of allyl alcohols induces strong carbon shifts, shielding γ and deshielding δ effects. These shifts are a consequence of through‐bond polarization of the olefinic carbons. Allyl ethers show similar, but milder perturbations. The olefinic carbon shifts reveal a strong concentration dependence. This effect, in greatly reduced form, is also observed in non‐oxygenated alkenes. Hydrogen bonding by alcohols enhances the chemical shift difference in olefinic carbon pairs by increased polarization.

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