
%0 Journal Article
%A Warrener, RN 
%A Evans, DAC 
%A Paddon-Row, MN 
%A Russell, RA 
%T The regiospecific cycloaddition of 8,8-dimethylisobenzofulvene with isobenzofuran, 1-methylisobenzofuran and 1,3-dimethylisobenzofuran
%J Australian Journal of Chemistry
%D 1982/04/01
%V 35
%N 4
%P 757-766
%K 
%R https://doi.org/10.1071/CH9820757
%U https://www.publish.csiro.au/paper/CH9820757 
%X The mixed 1 : 1 adduct formed upon reaction of isobenzofuran with 8,8-dimethylisobenzofulvene is shown to have structure (5) resulting from a [10 + 8] cycloaddition in which the isobenzofulvene serves as the 10 &#960; reagent and the isobenzofuran as the 8 &#960; reagent. The reaction occurs stereospecifically and forms exclusively the endo adduct. Lanthanide-induced shift spectroscopy, 13C n.m.r. and 1H n.m.r. spectroscopy, and deuterium-labelling techniques have been used to establish this structure. The structure of the adducts (24) and (26) derived from 1-methylisobenzofuran and 1,3-dimethylisobenzofuran, respectively, have also been established. A PMO treatment of this reaction correctly predicts the structure of these products including the regiochemistry of the product (24) formed from 1-methylisobenzofuran. 
