ISSN:
0030-4921
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A detailed study has been made on the 1H nuclear magnetic resonance (NMR) spectra of 5,6-dicarboxy-2-norbornene derivatives, whose chemical shifts and geminal, vicinal and long-range spin-spin coupling constants were determined. Each signal of the spectra of these derivatives shows a slight low-field shifts compared with norbornene itself. In the case of five methyl esters studied in this work, the signal of the 7s-proton remains at approximately the same position in all the compounds, but that of the 7a-proton is more variable. For the chemical shifts of the 7a-proton of the five methyl esters, an additive rule seems to hold: that the magnitude of the low-field shift, from the 7a-signal of norbornene itself, is obtained by adding each of the effects of the carboxyl and the carbomethoxy groups substituted at the endo-5-(or 6-) or the exo-5-(or 6-) positions of the norbornene ring. In most of the derivatives considered in this work, the spin-spin coupling constants, except those between bridgehead and bridged methylene protons, are about 1 to 2 Hz smaller than those of many other norbornene derivatives already studied. This fact seems to suggest that norbornenes, which have two bulky adjacent substituents at 5- and 6-positions, may suffer distortions in the norbornene ring.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1270010508
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