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The nuclear magnetic resonance spectrum of protopine: Rate of racemization and ring inversion

โœ Scribed by F.A.L. Anet; Mary A. Brown

Book ID
104240890
Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
142 KB
Volume
8
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The n.'m.r. spectrum (1) of protopine (I) has been assigned on the basis of rapid ring inversion in the ten-membered ring. However, the bands of the methylene protons in that ring are somewhat broader than expected. The broadness of the long-range coupling, but there may also be a contribution inversion is, in fact, not very fast. lines may be due in part to unresolved from incomplete averaging if ring d Contribution No. 2123, from the Department of Chemistry, UCLA.

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The energy barriers to ring inversion of 3,5,7-cyclooctatrienone (I) (11, and ~i~-l,2-dibromo-3,5,jr-cyclooctatriene (II) (2) have been determined by proton magnetic resonance (pmr) spectroscopy. We wish to report that the parent compound, 1,3,5-cyclooctatriene (III)\*, has an appreciably lower inve