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Communication | Regular issue | Vol 57, No. 7, 2002, pp.1211-1217
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9479
Effects of Base, Electrophile, and Substrate on the Selective Alkylation of Heteroaromatic Systems

Thomas E. Smith,* Michelle S. Mourad, and Alan J. Velander

*Department of Chemistry, Williams College, 47 Lab Campus Drive, Williamstown, MA 01267-2692, U.S.A.

Abstract

Several heteroaromatic systems, including oxazoles, pyrazoles, and thiophenes, are regioselectively alkylated using lithium diethylamide. Effects of substrate, base, and electrophile on the selectivity of this process are surveyed and interpreted.