INVESTIGADORES
POSTIGO Jose Alberto
artículos
Título:
A Novel Type of Nucleophilic Substitution Reactions on NonActivated Aromatic Compounds and Benzene itself with Trimethylsiliconide Anions
Autor/es:
JOSE ALBERTO POSTIGO; A ROSSI, ROBERTO
Revista:
ORGANIC LETTERS
Editorial:
American Chemical Society
Referencias:
Lugar: American Chemical Society-DOI: 10.1021/ol015666s; Año: 2001 vol. 3 p. 1197 - 1200
ISSN:
1523-7060
Resumen:
The reaction of fluorobenzene with Me3Si- anion (1) in HMPA at room temperature surprisingly affords o- and p-fluorotrimethylsilylbenzenes (substitution of aromatic H for TMS, 76% yield) 7a and 7b and also 14% of trimethylsilylbenzene (2). Benzene itself reacts at 50 °C to furnish 4 in 45% yield. Pyridine affords p-trimethylsilylpyridine quantitatively. Mechanistic studies are presented.
