193904-81-3Relevant articles and documents
γ-Regioselective reaction of metaloxysilyl-substituted allyllithium derived from allyldiphenylsilanol
Takaku, Koji,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 5189 - 5192 (1997)
Treatment of allyldiphenylsilanol (1) with two equivalents of butyllithium in the presence of HMPA at -45°C afforded silylallyllithium 2a bearing an oxide anion on the silicon atom. The reaction of 2a with various electrophiles gave γ-products selectively in good yields. Higher regio- and stereoselectivities were achieved in the reaction of silyl-substituted allyllithium derived from potassium allylsilanolate with butyllithium.
Facile Preparation of Vicinal Allylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
Shinokubo, Hiroshi,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2255 - 2263 (2007/10/03)
Treatment of 2-(allyldimethylsiloxy)-1,1-dibromoalkane, which was easily prepared by an addition of aldehyde to an ethereal solution of (allyldimethylsilyl)dibromomethyllithium, with tributyltin hydride in the presence of catalytic amount of triethylborane afforded l-oxa-2-silacycloheptane derivative selectively in good yield. On the other hand, cyclization of vinyldimethylsiloxy derivative resulted in a formation of 3-methyl-1-oxa-2-silacyclopentane. An addition of allyldiphenylsilanol to ethyl vinyl ether in the presence of N-iodosuccinimide provided l-(allyldiphenylsiloxy)-l-ethoxy-2-iodoethane, which was also converted into a seven-membered ring product upon treatment with tributyltin hydride.
