INVESTIGADORES
SILBESTRI Gustavo Fabian
artículos
Título:
Synthesis of Arylstannanes from Arylamines
Autor/es:
A.B. CHOPA; M.T. LOCKHART; G.F.SILBESTRI
Revista:
ORGANOMETALLICS
Editorial:
The American Chemical Society
Referencias:
Lugar: Cambridge; Año: 2001 vol. 20 p. 3358 - 3360
ISSN:
0276-7333
Resumen:
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.