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The 1H NMR spectra of exo- and endo-3-thiatricylo[4.2.1.02,5]non-7-ene 3,3-dioxide. The shielding effect of the sulfone group

✍ Scribed by H.-D. Martin; R. Iden; D. Scheutzow; L. M. Jackman

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
591 KB
Volume
14
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The proton spectra of exo‐ and endo‐3‐thiatricyclo[4.2.1.0^2,5^]non‐7‐ene 3,3‐dioxide have been analysed and completely assigned. Considerations of coupling constants indicate that the thietane ring is nonplanar and that the norbornene residue is significantly distorted from the geometry of norbornene itself. The sulfone group induces significant changes in the shielding of the proximate olefinic proton in the endo isomer and the bridge protons in the exo isomer. These shifts appear to be the result of the electrostatic effects and effects associated with the diagmagnetic anisotropy of the sulfone group.

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