Open AccessThe Diels–Alder reaction of 4-methoxy-7-hydroxyisobenzofuran with methyl vinyl ketone; a general method for identification of some regioisomeric α-naphthols
Author(s) -
Brian A. Keay,
R. Rodrigo
Publication year - 1985
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v85-121
Subject(s) - chemistry , methyl vinyl ketone , ketone , aromatization , adduct , isobenzofuran , diels–alder reaction , medicinal chemistry , organic chemistry , proton nmr , carbon 13 nmr , stereochemistry , catalysis
Two regioisomeric α-naphthols 14 and 15 obtained by aromatization of the methyl vinyl ketone adducts of an unsymmetrical isobenzofuran 9 are differentiated from each other by the observation of significant upfield shifts of the peri proton resonances in the 1 H nmr spectra of their acetates 16 and 17. Such upfield shifts of 0.3–0.6 ppm appear to be a general phenomenon and are probably due to the anisotropic effect of the acetate carbonyl group.