Epoxidation versus Allylic Oxidation (CH Insertion) in the Oxyfunctionalization of Vinylsilanes and β-Hydroxy Derivatives by Dimethyldioxirane
Epoxidation of acyclic vinylsilanes by dimethyldioxirane affords α,β-epoxysilanes in high yields, whereas for cyclic vinylsilanes appreciable amounts of allylic oxidation is observed.These competitive pathways become more pronounced, when the reactivity of the double bond is decreased by electronic and/or steric factors.
Adam, Waldemar,Prechtl, Frank,Richter, Markus J.,Smerz, Alexander K.
p. 4991 - 4994
(2007/10/02)
AN EFFICIENT METHOD FOR PREPARATION OF TRIMETHYLSILYL ETHYLENE OXIDE AND SOME OTHER TRIMETHYLSILYL OXIRANES
Trimethylsilyl ethylene oxide and other α,β-epoxysilanes were obtained from corresponding (trimethylsilyl)alkenes by an one-pot procedure involving successive treatment with N-bromosuccinimide and aqueous sodium hydroxide.
Jankowski, P.,Masnyk, M.,Wicha, J.
p. 873 - 880
(2007/10/02)
THE STEREOSELECTIVE CONVERSION OF VINYLSILANES TO γ-SUBSTITUTED ALLYLSILANES VIA HIGHER ORDER CUPRATES
Pure cis-vinylsilanes are efficiently converted to cis-epoxysilanes which react smoothly with Li2Cu(CN)(CH2TMS)2 to provide the corresponding eryhro disilylated alcohol, in excellent yield and isomeric purity.Elimination of the elements of TMSOH affords e
Soderquist, John A.,Santiago, Braulio
p. 5693 - 5696
(2007/10/02)
THE REACTION OF α,β-EPOXYSILANES WITH METALLATED ALKYLARYL SULPHONES. A NOVEL APPROACH TO ALLYLIC ALCOHOLS
Lithiated alkylaryl sulphones (2a-c) react with α,β-epoxysilane (1) to yield O-trimethylsilyl allylic alcohols (3a-c), predominantly as Z isomers.The BF3-assisted reaction followed by treatment of the adduct with nBu4NF affords allylic alcohols.
Masnyk, Marek,Wicha, Jerzy
p. 2497 - 2500
(2007/10/02)
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