Nuclear Magnetic Resonance Studies of Bicyclic Thiophene Derivatives. II. Through Space H–F Coupling in <i>o</i>-Fluorophenyl Derivatives of Benzoylthiophene, Thienopyrimidine and Thienodiazepine Derivatives

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Published
1975-03-01
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  • https://academic.oup.com/pages/standard-publication-reuse-rights
DOI
  • 10.1246/bcsj.48.974
Publisher
Oxford University Press (OUP)

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<jats:title>Abstract</jats:title> <jats:p>Proton–fluorine coupling over six bonds has been observed between fluorine and Hβ of the thiophene ring in ortho fluorophenyl derivatives of 4-phenylthienopyrimidines (1), 2-acetylamino-3-benzoylthiophenes (2), 5-phenyl-1,4-thienodiazepines (3) and 5-phenyl-1,4-thienodiazepine-4-oxides (4). The solvent effect and the N-methylation effect on the coupling constant can be explained by considering that the H–F coupling is a through space coupling. The value of coupling constant (JHF: 0.5 Hz to 4.1 Hz) depends upon the geometry of the ring system condensed at 2-C and 3-C of thiophene ring, decreasing in the order of 1&gt;2&gt;3&gt;4. A discussion is given on the manner of steric repulsion between the benzene ring and some atoms on the other moiety of these compounds.</jats:p>

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