Studies on Organometallic Compounds. II. Facile and Convenient Method for the Synthesis of Iodoazines through Iododestannation of Trimethylstannylazines

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Trimethylstannyl and bis (trimethylstannyl) derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethylstannyl sodium, which was generated in situ from chlorotrimethyl-stannane and sodium. These stannyl derivatives readily underwent iododestannation on treatment with iodine to produce the corresponding iodo and diiodo derivatives of pyridine, quinoline, and isoquinoline, respectively, in good yields.