Tetrahedron letters

Single and double reductive cleavage of C O bonds of aromatic dimethyl acetals and ketals: Generation of benzylic mono-and dicarbanions

U Azzena, G Melloni, L Pisano, B Sechi

Index: Azzena; Melloni; Pisano; Sechi Tetrahedron Letters, 1994 , vol. 35, # 36 p. 6759 - 6762

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Citation Number: 17

Abstract

Abstract The reductive cleavage of aromatic dimethyl acetals and ketals, 1, with Li metal in THF at low temperature allows the generation of stable α-alkoxy-α-arylsubstituted carbanions, avoiding the Wittig rearrangement. Reaction of these carbanions with various electrophiles afforded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.

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