66885-88-9

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 930-68-7 cyclohexenone 
• 5804-85-3 diethylaluminium cyanide 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 25017-78-1 3-cyano-2-cyclohexenone 
• 112496-83-0 2-methylene 3-oxo cyclohexane carbonitrile 
• 112496-80-7 3-oxo 2-phenylsulfonylmethyl cyclohexane carbonitrile 
• 112496-77-2 3-oxo 2-phenylthiomethyl cyclohexane carbonitrile 

Relevant academic research and scientific papers

A Tin-tungsten mixed oxide as an efficient heterogeneous catalyst for C-C Bond Bond-Forming reactions

The tin-tungsten mixed oxide prepared by the calcination of the tin-tungsten hydroxide precursor with a Sn/W molar ratio of 2 at 800 °C (SnW2-800) acts as an effective and reusable solid catalyst for C-C bond-forming reactions, such as the cyclization of citronellal, the Diels-Alder reaction, and the cyanosilylation of carbonyl compounds with trimethylsilyl cyanide (TMSCN). Various kinds of structurally diverse aliphatic, aromatic, and unsaturated, heteroatom-containing substrates could be converted into the desired products in high to excellent yields. The observed catalyses for these reactions were truly heterogeneous and the recovered catalyst could be reused several times without an appreciable loss of its high catalytic performance. The Bronsted acid sites generated on the aggregated polytungstate species on SnW2-800 likely play an important role in the C-C bond-forming reactions.

Hydrosilylation of ketone and imine over poly-N-heterocyclic carbene particles

N-Heterocyclic carbene (NHC)-catalyzed ketone/imine hydrosilylation, silane alcohol condensation and asymmetric ketone hydrosilylation reactions were demonstrated for the first time over solid, main-chain poly-NHC particles. The stable and robust poly-NHC

An immobilized organocatalyst for cyanosilylation and epoxidation

An immobilized organocatalyst has been synthesized by covalently anchoring an N-octyldihydroimidazolium hydroxide fragment onto SiO2 (denoted as 1-OH/SiO2). This catalyst exhibits high catalytic performance for the cyanosilylation of

Oxidation of silyl enol ethers by using IBX and IBX·N-oxide complexes: A mild and selective reaction for the synthesis of enones

α,β-Unsaturated carbonyl compounds can be prepared by the oxidation of trimethylsilyl enol ethers with IBX (1) or IBX·MPO (2). A diverse set of carbonyl compounds can be dehydrogenated with ease by using this method. Trimethylsilyl enol ethers such as 4, which are formed in situ by the addition of an organometallic species to an enone, can be dehydrogenated with 1 or 2 to give a functionalized enone (e. g. 3 → 5). IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.

Solid Acid and Base-Catalyzed Cyanosilylation of Carbonyl Compounds with Cyanotrimethylsilane

A new attempt was investigated to utilize inorganic solid acids and bases for the promotion of the reaction of cyanotrimethylsilane (Me3SiCN) with carbonyl compounds.Strongly acidic solids, such as Sn4+ ion-exchanged montmorillonite (Sn-Mont) and Fe3+ ion-exchanged montmorillonite (Fe-Mont), as well as basic solids, such as calcium fluoride (CaF2), hydroxyapatite (HAp), calcium oxide (CaO), and magnesium oxide (MgO), catalyzed the reaction of Me3SiCN with aldehydes and ketones to afford the corresponding 2-(trimethylsiloxy)alkanenitriles in good yields.The reactions of dimethyl acetals with Me3SiCN in the presence of solid acids afforded 2-methoxyalkanenitriles.In cyanosilylation of α,β-unsaturated ketones two kinds of adducts were produced selectively, depending on the use of a solid acid or a solid base: 1,4-Adducts (trimethylsilyl enol ether forms) were selectively obtained in the presence of strong solid acids, such as Fe-Mont and Sn-Mont, while 1,2-adducts (trimethylsilyl ether forms) were predominantly formed in the presence of solid bases, such as HAp, CaO, and MgO.The solid acids and bases realized higher activities and selectivities in the cyanosilylation than did conventional homogeneous catalysts.

Efficient and Regioselective Cyanosilylation of Cyclohex-2-enone and Other Unsaturated Ketones over Solid Acid and Base Catalyst

Cyanotrimethylsilane reacts with α,β-unsaturated ketones to afford 1,4- and 1,2-adducts regioselectively in the presence of strongly acidic montmorillonite and strongly basic CaO or MgO, respectively.

SYNTHESES OF NITRILE AND METHYL ESTER CORRESPONDING TO (dl)-SARKOMYCIN AND OF RELATED COMPOUNDS.

Nitrile 6a and ester 12 corresponding to (dl)-sarkomycin, 6- and 7-membered rings analogue nitriles 6b, 6c, and 3-methyl substituted nitrile 6d were prepared.Conjugate addition of cyanotrimethyl silane to cyclic α-enones gave 3-trimethylsiloxy 2-cycloalkene carbonitriles.Their alkylation with chloromethyl phenyl sulfide followed by oxone oxidation to sulfones and sulfinic acid elimination on basic alumina led to α-methylene carbonyl compounds.Obtention of the ester 12 involved acetalization of 3-oxo 2-phenylthiomethyl cyclopentane carbonitrile, basic hydrolysis into acid, deacetalization, esterification, oxidation and elimination of sulfinic acid.

CYANOTRIMETHYLSILANE AS A VERSATILE REAGENT FOR INTRODUCING CYANIDE FUNCTIONALITY

Cyanotrimethylsilane adds to some α,β-unsaturated ketones in conjugate manner under the catalytic action of Lewis acids such as triethylaluminium, aluminium chloride, and SnCl2.Hydrolysis of the products gives β-cyano ketones which are identical to the hydrocyanated products of the starting enones.The title silicon reagent reacts with acetals and orthoesters under the catalytic action of SnCl2 or BF3*OEt2 affording 2-alkoxy- and 2,2-dialkoxyalkanenitriles.Application of the reaction to O-protected β-D-ribofuranoses gives selectively β-D-ribofuranosyl cyanide in excellent yield.

TRIMETHYLSILYL TRIFLATE IN ORGANIC SYNTHESIS

Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media.The reactions proceed via one-center, electrophilic coordination of the silyl group to hetero functional groups and exhibit unique selectivities.