Reactions of (Triphenylsilyl)ethylene Oxide with Grignard Reagents (and with MgBr(2)). A Reinvestigation.
Reactions of (triphenylsilyl)ethylene oxide (1) with simple Grignard reagents such as EtMgBr and PhMgBr have been reported to yield crystalline hydroxysilanes assigned as the alpha-hydroxy silanes expected from beta opening of the epoxide. Reinvestigation of these reactions showed that the hydroxysilanes were the beta-hydroxy silanes 4 and 7 expected from a rearrangement-trapping sequence; a bromohydrin, assigned as the alpha-bromo-beta-hydroxy silane 9 from alpha opening, and (triphenylsilyl)acetaldehyde (8) were also formed.
Hudrlik
Paul F.
PF
Department of Chemistry, Howard University, Washington, D.C. 20059.
Ahmed
Mohamed E.
ME
Roberts
Ralph R.
RR
Hudrlik
Anne M.
AM