71009-12-6

Basic information

• Product Name: Silane, (1,1-dimethylethyl)[[4-(1,1-dimethylethyl)cyclohexyl]oxy]dimethyl-, cis-
• CAS NO: 71009-12-6
• Molecular Formula: C16H34OSi
• Molecular Weight: 270.531
• Mol File: 71009-12-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Silane, (1,1-dimethylethyl)[[4-(1,1-dimethylethyl)cyclohexyl]oxy]dimethyl-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (1,1-dimethylethyl)[[4-(1,1-dimethylethyl)cyclohexyl]oxy]dimethyl-, cis-(71009-12-6)
• EPA Substance Registry System: Silane, (1,1-dimethylethyl)[[4-(1,1-dimethylethyl)cyclohexyl]oxy]dimethyl-, cis-(71009-12-6)

Safety Data

• Hazardous Substances Data: 71009-12-6(Hazardous Substances Data)

Upstream product

• 66323-98-6 tert-butyl(4-tert-butylcyclohex-1-enyloxy)dimethylsilane 
• 29681-57-0 tert-butyldimethylsilane 
• 98-53-3 4-tercbutyl-cyclohexanone 

Relevant articles and documents

Ionic Hydrogenation with Organosilanes under Acid-Free Conditions. Synthesis of Ethers, Alkoxysilanes, Thioethers, and Cyclic Ethers via Organosylil Iodide and Triflate Catalyzed Reductions of Carbonyl Compounds and Their Derivatives

The general ether synthesis method based on the trialkylsilane/trialkylsilyl iodide or triflate reagent system has been extended to the syntheses of alkoxysilanes from ketones, tetrahydrofurans and tetrahydropyrans from dicarbonyl compounds, and thioethers by reductive cleavage of O-silylhemithioacetals.

Hydrosilylation of carbonyl-containing substrates catalyzed by an electrophilic η1-silane iridium(III) complex

Hydrosilylation of a variety of ketones and aldehydes using the cationic iridium catalyst (POCOP)Ir(H)(acetone)+, 1 (POCOP = 2,6-bis(di-tert-butylphosphinito)phenyl), is reported. With triethyl silane, all but exceptionally bulky ketones undergo quantitative reactions employing 0.5 mol % catalyst in 20-30 min at 25 °C. Hydrosilylation of esters and amides results in over-reduction and cleavage of C-O and C-N bonds, respectively. The diastereoselectivity of hydrosilylation of 4-tert-butyl cyclohexanone has been examined using numerous silanes and is highly temperature dependent. Using EtMe2SiH, analysis of the ratio of cis:trans hydrosilylation products as a function of temperature yields values for ΔΔH ? (ΔH?(trans) - ΔH ?(cis)) and ΔΔS? (ΔS ?(trans) - ΔS?(cis)) of -2.5 kcal/mol and -6.9 eu, respectively. Mechanistic studies show that the ketone complex (POCOP)Ir(H)(ketone)+ is the catalyst resting state and is in equilibrium with low concentration of the silane complex (POCOP)Ir(H)(HSiR 3)+. The silane complex transfers R3Si + to ketone, forming the oxocarbenium ion R3SiOCR' 2+, which is reduced by the resulting neutral dihydride 3, (POCOP)Ir(H)2, to yield product R3SiOCHR'2 and (POCOP)IrH+, which closes the catalytic cycle.