The acetal 1 reacts with 1 equiv of alkyllithium in the presence of catalytic diiipropylamine to form isobenzofuran (2), which with an additional equivalent of alkyllithium gives 1- lithioisobenzofuran (3). Solutions of 3 have been treated with various electrophiles and the resulting products characterized by NMR and as cycloadducts formed on addition of dienophiles. Lithiation of 2 occurs cleanly at C-1, as shown by quenching with DzO. Both ...
