Arylamines have been converted into aryltrimethylammonium salts, which on reaction with sodium trimethylstannide (1) in liquid ammonia afford aryltrimethylstannanes by the S RN 1 mechanism. With (4-methoxyphenyl)-(2), (1-naphthyl)-(4), phenyl-(6), (4-acetylphenyl)-(8), and (4-cyanophenyl)trimethylammonium salts (10) the substitution products are obtained in good to excellent yields (45-100%). Also, the photostimulated reaction of (2-pyridyl)trimethylammonium iodide (12) with 1 leads to the substitution product 13 (50%). With (4-chlorophenyl)trimethylammonium iodide (14) the disubstitution product 19 is obtained in 76% yield. On the other hand, the results obtained in the reaction of (4-bromophenyl)trimethylammonium iodide (15) with 1 clearly indicate a fast HME reaction in the dark. The ET process (S RN 1) competes, although inefficiently, under irradiation.

Phenols are converted into aryl diethyl phosphates, which on reaction with alkali-metal triorganostannides in liquid ammonia afford arylstannanes in excellent yield.