66255-13-8

Upstream product

• 63031-67-4 4-(1,1-dimethylethyl)cyclohexen-1-yltrimethylsilane 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 6832-09-3 1-chloro-4-tert-butylcyclohexene 

Downstream Products

• 60640-81-5 4-(2-methylpropyl)-1e-(trimethylsilyl)cyclohexanol 
• 66228-07-7 4-(2-methylpropyl)-1a-(trimethylsilyl)cyclohexanol 
• 66228-04-4 cis-1-(trimethylsilyl)-trans-4-tert-butylcyclohexan-2-ol 
• 66228-04-4 cis-1-(trimethylsilyl)-cis-4-tert-butylcyclohexan-2-ol 
• 73872-67-0 1-(trimethylsilyl)-2-deuterio-4-tert-butylcyclohexanol 
• 73872-59-0 C₁₃H₂₇⁽²⁾HOSi 
• 73872-59-0 C₁₃H₂₇⁽²⁾HOSi 
• 66227-98-3 t-4-t-butyl-r-1-trimethylsilyl-7-oxabicyclo<4.1.0>heptane 
• 142743-99-5 r-5-tert-Butyl-t-2-(trimethylsilyl)cyclohex-t-yl p-nitrobenzoate 
• 142743-99-5 r-5-tert-Butyl-c-2-(trimethylsilyl)cyclohex-c-yl p-nitrobenzoate 
• 73872-60-3 4-tert-butyl-1-deuteriocyclohexene 

Relevant academic research and scientific papers

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.

Some Epoxide Ring-opening Reactions of αβ-Epoxysilanes

Epoxide ring-opening of 1,2-epoxy-1-trimethylsilylcyclohexane (3) has given a range of the 2-substituted 2-trimethylsilylcyclohexanols (4; X = H, OH, OMe, OCH2CH=CH2, Br, I, SCN) in which attack by nucleophile has occured at the carbon α to silicon.The products (4) have been transformed into a number of functionalised silanes, including the silyl-episulphide (9).Other epoxides which have been less extensively studied are the conformationally biased epoxysilanes (10) and (11), the eight-membered ring epoxysilanes (17) and (21) and the two stereoisomeric 2,3-epoxy-3-trimethylsilylpentanes (26) and (29).Epoxide ring-opening adducts were obtained after treatment with H+-MeOH in all cases except for compound (17), where the bicyclic alcohol (18) was formed by a transannular reaction.

Silanes in Organic Synthesis. 9. Enesilylation as a Method for 1,2-Carbonyl Migration within Ketones and for Conversion to 1,2-Transposed Allylic Alcohols

Vinylsilanes are shown to be valuable synthetic intermediates in useful transformations of ketones.The epoxidation of vinylsilanes followed by lithium aluminium hydride reduction and oxidation with chromic acid and sulfuric acid in a two-phase (ether/water) system often gives high yields of 1,2-transposed ketones.With singlet oxygen and sequential sodium borohydride reduction, 2-trimethylsilyl alcohols are produced in which the α position of the parent ketone has been regiospecifically oxygenated.Fluoride ion promoted desilylation completes the conversion to the migrated allylic alcohol.