Cleavage of silicon-vinyl carbon bond by nBu4NF

✍ Scribed by Hiroji Oda; Mitsuyoshi Sato; Yoshitomi Morizawa; Koichiro Oshima; Hitosi Nozaki

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 228 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88048-x

✦ Synopsis

DimethyZphenyZsiZyZ-and diphenyZmethyZsiZyZ-vinyl carbon bonds are cleaved with ni3uqNF. DesiZyZation of I-phenyZthio-l-trimethyZsiZyZ-lalkenes in the presence of aldehyde moiety gives carbanion adducts. The affinity of fluoride ion for silicon has been well recognized and widely used for the cleavage of silicon-carbon bond. 1 Chan has reported that the cleavage of trimethylsilyl-vinyl carbon bonds is, however, difficult or impossible under ordinary conditions. 2 In connection with our new synthesis of vinylsilanes, 3 we have reexamined the cleavage of vinylsilanes. Surprisingly, "Bu4NF has proved to be effective for the cleavage of PhMe2Siand Ph2MeSi-vinyl carbon bonds. Not only special vinylsilanes 2,4 having the hydroxyl group at 8-carbon but also prosaic ones were cleaved efficiently.