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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.


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.