In the Ir-deficient aromatic series, such as pyridine or quinoline, few successful metalations of monoalkoxy derivatives have been reported. Metalation is only possible when there is an activated po~ ition'~ J~ J~ or when no competitive addition can occur. 3o Thus, for example, 3-ethoxypyridine undergoes metalation at the 2-position12 when n-butyllithium-TMEDA chelate in tetrahydrofuran (THF) at-40 OC is used.