Ortho and para-diethylphosphonotoluenes are regioselectively lithiated using lithium diisopropylamide in tetrahydrofuran at -70 degrees C at the benzylic positions. The lithiated species react with para-anisaldehyde or chlorotrimethylsilane to give the corresponding carbinols or trimethylsilylated derivatives in excellent yields. In contrast, the extent of metallation of meta-diethylphosphonotoluene does not exceed 60% under the same conditions.