The Journal of Organic Chemistry

Preparation of muconic acid anhydrides. Characterization of the 1-oxacyclohepta-3, 5-diene-2, 7-dione structure

TR Demmin, MM Rogic

Index: Demmin, Timothy R.; Rogic, Milorad M. Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 1153 - 1156

Full Text: HTML

Citation Number: 36

Abstract

4 4a a substantial contribution from resonance structure 4a to the overall electronic description of the molecule. With the increased double bond character at the methoxy oxygen, homoallylic type coupling may be effectively transmitted. Long-range coupling,-0.4 Hz, is also present in the analogous o-benzoquinone 3 where similar resonance may exist. However, in the related 3-methoxy-5-tert-b~-tylcatechol (7), with no resonance possible as ...