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Carbon-13 NMR spectra of some epoxides derived from dicyclopentadiene

✍ Scribed by Yasuhiro Matoba; Takashi Kagayama; Yasutaka Ishii; Masaya Ogawa


Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
335 KB
Volume
17
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

The ^13^C NMR spectra of a series of epoxides derived from endo‐ and exo‐dicyclopentadiene and their partially hydrogenated compounds were determined to examine the substituent effects arising from the introduction of the oxirane ring in comparison with those found in other ring systems. The ^13^C signals of some epoxides were assigned by using lanthanide shift reagents. Characteristic substituent effects exerted by an oxirane ring were demonstrated. Marked steric γ‐effects of −8—13 ppm were observed at the bridge carbon signal in the bicyclo[2.2.1]heptane skeleton. Differences were found in the substituent effects between endo‐ and exo‐dicyclopentadiene epoxides, and have been discussed in relation to the molecular geometry.


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