114701-66-5

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 4364-06-1 (E)-cinnamaldehyde dimethylacetal 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 

Downstream Products

• 100573-32-8 2-Cyan-2-methoxy-4-phenyl-3-butensaeure-ethylester 
• 100573-31-7 2-Methoxy-4-phenyl-2-pentennitril 
• 100573-30-6 2-Methoxy-2-methyl-4-phenyl-3-butennitril 
• 100573-20-4 C₁₁H₁₀LiNO 

Relevant academic research and scientific papers

A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters

The cyanation of acetals and orthoesters by using a sterically congested α-cyanoamine as a cyanating reagent was investigated. The α-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Analysis of the reaction mixture by 1H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate.

Effects of phosphorus substituents on reactions of α- alkoxyphosphonium salts with nucleophiles

The effects of phosphorus substituents on the reactivity of α-alkoxyphosphonium salts with nucleophiles has been explored. Reactions of α-alkoxyphosphonium salts, prepared from various acetals and tris(o-tolyl)phosphine, with a variety of nucleophiles proceeded efficiently. These processes represent the first examples of high-yielding nucleophilic substitution reactions of α-alkoxyphosphonium salts. The reactivity of these salts was determined by a balance between steric and electronic factors, respectively, represented by cone angles θ and CO stretching frequencies ν (steric and electronic parameters, respectively). In addition, a novel reaction of α-alkoxyphosphonium salts derived from Ph3P with Grignard reagents was observed to take place in the presence of O2 to afford alcohols in good yields. A radical mechanism is proposed for this process that has gained support from isotope-labeling and radical-inhibition experiments. A dramatic change in the reactivity of an α-alkoxyphosphonium salt toward nucleophiles is observed due to the steric and electronic nature of the phosphine substituents. By changing the type of phosphorus substituents, the reaction pathway can be controlled to proceed selectively by substitution or a new radical reaction (see scheme; OTf=trifluoromethansulfonate, TMS=trimethylsilyl, o-tol=tolyl). Copyright

High-pressure-promoted uncatalyzed cyanation of acetals using trimethylsilyl cyanide as a cyanide source in nitromethane

A new uncatalyzed method for the preparation of cyanohydrin O-alkyl ethers was developed using the high-pressure-promoted reaction of acetals with trimethylsilyl cyanide in nitromethane. Georg Thieme Verlag Stuttgart.

Polymer-supported dicyanoketene acetal as a π-acid catalyst: Monothioacetalization and carbon-carbon bond formation of acetals

Polymeric dicyanoketene acetals (DCKA) were synthesized by copolymerization of styrene and divinylbenzene or ethylene glycol dimethacrylate. These novel polymers could be used successfully as recyclable π-acid catalysts in monothioaCetalization or carbon-carbon bond forming reaction of acetals.

Carbon-carbon bond formation and reduction of aldehydes, ketones and acetals with silylated nucleophiles catalysed by tetracyanoethylene

Tetracyanoethylene catalyses the reactions of aldehydes, ketones and acetals with silylated nucleophiles such as trimethylsilyl cyanide, allyltrimethylsilane, aryl methyl ketone trimethylsilylenol ethers and triethylsilane to promote carbon-carbon bond formation and reduction under neutral conditions.All the evidence strongly suggested that the reactions occur through single electron transfer (SET) mechanism based on UV spectroscopic measurements.

Catalytic Activity of Tetracyanoethylene in the Reactions of Aldehydes, Ketones and Acetals with Silylated Nucleophiles

Tetracyanoethylene catalyses the reactions of aldehydes, ketones and acetals with silylated carbon and hydrogen-nucleophiles to promote carbon-carbon bond formation and reduction under neutral conditions.

Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of 2 and TMS-CN under Almost Neutral Conditions

In the presence of catalytic amount of a transition metal compound such as 2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields.In the coexistence of catalytic amounts of Rh

Efficient Activation of Acetals toward Nucleophiles by the Use of Transition Metal Salts. New Method for Cyanation of Acetals and Orthoester Derived from Aromatic and α,β-Unsaturated Carbonyl Compounds with Trimethylsilyl Cyanide under Neutral Condition

In the presence of a catalytic amount of transition metal salts (NiCl2, CoCl2, PdCl2, etc.), trimethylsilyl cyanide smoothly reacts with acetals or orthoester derived from aromatic and α,β-unsaturated carbonyl compounds to give the corresponding α-cyano d

Efficient Activation of Acetals toward Nucleophiles with 2 Catalyst. New Method for the Preparation of Aldols from Acetals and Silyl Enol Ethers by the Combined Use of Catalytic Amounts of 2 and Trimethylsilyl Cyanide

In the presence of a catalytic amount of 2, di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium, trimethylsilyl cyanide smoothly reacts with acetals derived from aliphatic, unsaturated and aromatic aldehydes to form the corresponding α-cyano derivativ

New Method for Oxidative Carbon-carbon Bond Formation by the Reaction of Allyl Ethers, 2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) and Silyl Carbon Nucleophiles

Allyl ethers are oxidized by DDQ to generate the corresponding cationic species, which in turn react with silyl carbon nucleophiles in the presence of a catalytic amount of lithium perchlorate to afford the coupled products in a one-pot procedure in good