Introduction of an arylthio(trimethylsilyl)methyl group into arenes by friedel-crafts reaction: synthesis of arylmethyltrimethylsilanes

✍ Scribed by Hiroyuki Ishibashi; Hiroshi Nakatani; Yoshizumi Umei; Masazumi Ikeda

• Book ID: 104228890
• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 111 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)98738-0

✦ Synopsis

Friedel-Crafts reactions of [arylthio(chloro)methyl]trimethylsilanes (ti,&) with arenes gave [aryl(arylthio)methyl]trimethylsilanes (a,b>, which were converted into arylmethyltrimethylsilanes (3) by reduction with Raney nickel. Arylmethyltrimethylsilanes (3) are versatile intermediates in organic synthesis. 1 These compounds are generally prepareã by the reaction of arylmethylmagnesium halides with chlorotrimethylsilane. Here we wish to report an alternative simple method for the preparation of 2, which involves a Friedel-Crafts reaction of [arylthio(chloro)methyl]trimethylsilanes (&,b) with arenes and subsequent desulfurization of the resultant products <_,b)_ Lewis S.*