
TY  - JOUR
A1  - Warrener, RN 
A1  - Evans, DAC 
A1  - Paddon-Row, MN 
A1  - Russell, RA 
T1  - The regiospecific cycloaddition of 8,8-dimethylisobenzofulvene with isobenzofuran, 1-methylisobenzofuran and 1,3-dimethylisobenzofuran
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 4
SP  - 757
EP  - 766
KW  - 
UR  - https://doi.org/10.1071/CH9820757 
N2  - 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. 
ER  -

