14904-40-6

Upstream product

• 96-09-3 styrene oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 100-42-5 styrene 
• 614-16-4 Benzoylacetonitrile 
• 75-77-4 chloro-trimethyl-silane 
• 86208-59-5 3-trimethylsily;-4,5-dihydro-5-phenylisoxazole 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 100-52-7 benzaldehyde 
• 14904-37-1 Sodium acetonitrile 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 4360-47-8 cinnamonitrile 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 

Relevant academic research and scientific papers

Efficient ring opening of epoxides with trimethylsilyl azide and cyanide catalyzed by erbium(III) triflate

Epoxides can be opened under neutral conditions with TMSN3 and TMSCN in the presence of catalytic amounts of Lewis acid, affording the corresponding ring-opened compounds in high yields.

Ring opening of oxiranes catalyzed by Mn-Salen immobilized mesoporous materials

Mn-Salen Immobilized mesoporous materials were found to be efficient solid catalysts for the nucleophilic ring opening of oxiranes with TMSN3, TMSCN and aniline.

Zinc-promoted Reactions. Part 10.1 Reduction of α- and β-Cyano Ketones in Protic and Aprotic Systems

The difference courses of the zinc-promoted reductions of α- vs.β-cyano ketones in AcOH-Ac2O and CH3CN-CITMS can be interpreted according to a general mechanism.

Improved Synthesis of β-Trimethylsilyloxy Nitriles in a Solvent-free Reaction under Classical Heating or Microwave Activation

Trimethylsilylacetonitrile (2) reacts with several aldehydes 1 to afford β-trimethylsilyloxy nitriles 3 without solvent either under microwave irradiation or in an oil-bath, in the presence of adjusted catalytic amounts of piperidine; yields are equivalen

Calcined MgAlCO3-HT catalysed cyanosilylation of carbonyl compounds and nucleophilic ring opening of oxiranes using TMSCN

Nucleophilic addition of TMSCN to carbonyl compounds is found to be catalysed efficiently using hydrotalcite as a solid base. The catalyst is also found to be active in the nucleophilic ring opening of oxiranes giving high regioselectivity.

Ring Opening Reactions of Epoxides Catalyzed by Samarium Iodides

SmI2(THF)2 catalyzes the ring opening of epoxides by trimethylsilylazide, trimethylsilylcyanide and primary and secondary amines.High regioselectivities are observed in specific cases.

Reactivity of silylated compounds with active methylene under microwave irradiation in heterogeneous dry media; application to the alkali metal fluoride-mediated silyl-Reformatsky reaction

The condensation of trimethylsilylacetic compounds 2a, 2b, (nitrile, ester) and trimethylsilylmethylphosphonic esters 2c with aromatic aldehydes 1, in the presence of alkali metal fluorides (potassium, cesium) unsupported or supported on alumina, magnesium oxide or clay (montmorillonite K10), is achieved by solvent-free techniques in a domestic microwave oven.The factors governing the reaction selectivity are studied.The silyl-Reformatsky reaction takes place in the presence of dried fluoride and leads to the silylated compound 3, which can be subsequently hydrolyzed to 4.The latter can be dehydrated to give the alkene 5.Keywords - alkali metal fluoride / silyl-Reformatsky reaction / nucleophilic activation / inorganic solid supports / trimethylsilyl-acetic compounds / microwave irradiation

ALKALI METAL FLUORIDE MEDIATED SILYL-REFORMATSKY REACTION IN SOLID-LIQUID MEDIA; ACTIVATION BY MICROWAVES.

Condensation of trimethylsilylacetonitrile or ethyltrimethylsilylacetate with benzaldehyde, in the presence of dried alkali metal fluorides in heterogeneous media under microwaves leads readily to β-trimethylsilyloxynitrile or ester according to a Reformatsky type reaction.The later products could be hydrolyzed and dehydrated on the wet inorganic salt to give the corresponding alkenes.

Regiospecific and Chemoselective Ring Opening of Epoxides with Trimethylsilyl Cyanide-Potassium Cyanide/18-Crown-6 Complex

Trimethylsilyl cyanide with catalytic potassium cyanide/18-crown-6 complex opens epoxides regiospecifically to give 3-((trimethylsilyl)oxy) nitriles.The addition of cyanide occurs at the least substituted carbon.The reaction is chemoselective for monosubstituted epoxides due to the parrticipation of a pentavalent silicon species.