Reaction of chloromethyltrimethylsilane and chloromethyltrimethylstannane with lithium 2,2,6,6-tetramethylpiperidide

✍ Scribed by R.A. Olofson; Dennis H. Hoskin; Kenneth D. Lotts

• Book ID: 104245691
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 241 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94638-6

✦ Synopsis

Recently Magnus and coworkers reported the selective deprotonation of chloromethyltrimethylsilane (1) to the carbanion (1) with sec-butyllithium-TMEDA.l In the presence of aldehydes and ketones, 2 reacted to give a,&epoxysilanes (g), compounds of substantial preparative value.' MeSSiCH2C1 m [MeSSicHCl] m [MeSSiFH-TMEDA 1 THF 2 Cl [MeSSieH] 4 Otherwise 1 was comparatively stable to -40°C and then decomposed only slowly by pathways which did not include fragmentation to trimethylsilylcarbene (5).2 Failure to generate 4 by the -