Synthesis of arylstannanes from arylamines

Arylamines have been converted into aryl-trimethylammonium 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 clear ly indicate a fast HME reaction in the dark. The ET process (S(RN)1) competes, although inefficiently, under irradiation.