The Journal of Organic Chemistry

1-Lithio-and 1, 3-dilithioisobenzofuran: formation and reactions with electrophiles

SL Crump, B Rickborn

Index: Crump, Stephen L.; Rickborn, Bruce Journal of Organic Chemistry, 1984 , vol. 49, p. 304 - 310

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Citation Number: 22

Abstract

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 ...