Lithiation of 2‐Aryl‐2‐(chloroaryl)‐1,3‐dioxolanes and Its Application in the Synthesis of New ortho‐Functionalized Benzophenone Derivatives
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2-Aryl-2-(chloroaryl)-1,3-dioxolanes 4 were lithiated ortho to the ketal group of the chloroaryl ring by treatment with butyllithium in THF between −78 and 0 °C. The site selectivity of some of the deprotonation reactions was rationalized by the long-range effect of the 4-chloro substituent. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized benzophenone derivatives. Intramolecular competition between the aryl rings was observed in the lithiation of 2-(4-chlorophenyl)-2-(4-fluorophenyl)-1,3-dioxolane (4s). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)