Allylic Proton-Proton Coupling in Stereodefined Alkylidenecyclobutanes and Alkylidenecycopentanes | Zendy

William F. Bailey | Zendy; Timo V. Ovaska | Zendy

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Allylic Proton-Proton Coupling in Stereodefined Alkylidenecyclobutanes and Alkylidenecycopentanes

Author(s) -

William F. Bailey,

Timo V. Ovaska

Publication year - 2019

Publication title -

journal of the mexican chemical society

Language(s) - English

Resource type - Journals

ISSN - 2594-0317

DOI - 10.29356/jmcs.v53i3.996

Subject(s) - allylic rearrangement , dihedral angle , coupling (piping) , proton , plane (geometry) , chemistry , spectral line , crystallography , physics , materials science , molecule , geometry , nuclear physics , organic chemistry , mathematics , quantum mechanics , metallurgy , catalysis , hydrogen bond

Analysis of the 1 H NMR spectra of eight stereodefined alkylidenecycloalkanes allows determination of the magnitude of allylic coupling in these compounds. In contrast to the trend normally observed, the magnitude of transoid-allylic coupling was found to be invariably greater by ~0.5 Hz than the cisoid-allylic coupling. The larger transoid-allylic coupling may be attributed to the slightly smaller dihedral angle relating allylic =C-C-H plane with the C=C-C plane in the E-isomers.

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