Tetrahedron

Naphthalene-catalysed lithiation of 2-(chlorophenyl)-1, 3-dioxolanes: Generation of formyl-and acetyl-phenyllithium equivalents [1]

FF Huerta, C Gómez, M Yus

Index: Huerta, Fernando F.; Gomez, Cecilia; Yus, Miguel Tetrahedron, 1999 , vol. 55, # 13 p. 4043 - 4050

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Citation Number: 12

Abstract

The reaction of 2-(chlorophenyl)-1, 3-dioxolanes 1 with an excess of lithium powder and a catalytic amount of naphthalene (5 mol%) in the presence of different carbonyl compounds [tBuCHO, Et2CO,(CH2) 5CO, PhCOMe] as electrophiles (Barbier-type conditions) in THF at− 78° C leads, after hydrolysis with water at the same temperature, to the expected products 3, the corresponding intermediates involved being formyl-or acetyl-phenyl anion equivalents.