Regio- and stereospecific cleavage of silyl- and disilylepoxides with lithium diphenylphosphide.
Unsubstituted or alpha- and beta-C-substituted silylepoxides react stereospecifically with lithium diphenylphosphide, optionally followed by methylation, to give vinylphosphonium iodides or vinylphosphine oxides resulting from alpha-opening and silyl enol ethers, vinylsilanes or alpha-hydroxysilanes by beta-opening. On the other hand, alpha,beta- or alpha,alpha-disilylepoxides afforded beta-silyl vinylphosphine oxides or alpha-silylated silyl enol ethers by alpha- and beta-cleavage, respectively. All compounds are interesting synthons in organic chemistry.
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Departamento de Química Orgánica, Universidad de Valladolid, 47011 Valladolid, Spain.
González-Nogal
Ana M
AM
Sarmentero
M Angeles
MA
D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D018020:Lithium Compounds; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; C506627:lithium diphenylphosphide