Tetrahedron letters

Lithiation of 2-(chloroaryl)-2-methyl-1, 3-dioxolanes and application in synthesis of new ortho-functionalized acetophenone derivatives

G Lukács, M Porcs-Makkay, G Simig

Index: Lukacs, Gyula; Porcs-Makkay, Marta; Simig, Gyula Tetrahedron Letters, 2003 , vol. 44, # 15 p. 3211 - 3214

Full Text: HTML

Citation Number: 13

Abstract

2-(4-Chlorophenyl)-2-methyl-1, 3-dioxolane 2a was lithiated ortho to the ketal group by treatment with butyllithium in THF at 0° C. Related 2-aryl-2-methyl-1, 3-dioxolanes possessing a chlorine substituent at the meta position of the aryl group 2b, c were lithiated with butyllithium in THF at− 78° C at the position between the two directing groups. The lithio species thus generated were treated with various electrophiles to give ortho- ...