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Volume 18, Issue 3, Pages 469-483

1H and 13C NMR spectroscopic studies of half-esters from monohydrolysis of dialkyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates

Yoshikazu Hiraga1,2 and Satomi Niwayama1

1Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA
2Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan

Copyright © 2004 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


The structures of the half-esters from the monohydrolysis of (exo,exo)-, (endo,endo)-, and (endo,exo)-dialkyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates were determined by 1H and 13C NMR as well as 2D NMR spectra, and the complete spectral assignment has been made. After conversion of one of the carboalkoxy groups to a carboxyl group, different tendencies were observed for the differences in 1H and 13C NMR chemical shifts between half-esters and the corresponding diesters.