Science and Technology Production

Synthesis of Arylstannanes from Arylamines

Article

Authorship:

A.B. Chopa ; M.T. Lockhart ; SILBESTRI, GUSTAVO FABIAN

Date:

2001

Publishing House and Editing Place:

The American Chemical Society

Magazine:

ORGANOMETALLICS, vol. 20 (pp. 3358-3360) The American Chemical Society

Summary *

Arylamines have been converted into aryltrimethylammonium salts, which on reaction with sodium trimethylstannide (1) in liquid ammonia afford aryltrimethylstannanes by the SRN1 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 (SRN1) competes, although inefficiently, under irradiation. Information provided by the agent in SIGEVA