34039-84-4

Upstream product

• 100-52-7 benzaldehyde 
• 540-61-4 2-aminoacetonitrile 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 151-63-3 aminoacetonitrile neutral sulfate 
• 100-39-0 benzyl bromide 
• 3010-05-7 benzylaminoacetonitrile 

Downstream Products

• 32303-39-2 2-Benzylidenamino-3-methylmercaptocrotonitril 
• 32303-38-1 2-Benzylidenamino-3-methylmercaptocrotonitril 
• 37525-10-3 5-benzylidenamino-3H-thiazole-2-thione 
• 99984-46-0 benzylidene-(2-methoxy-thiazol-5-yl)-amine 
• 208041-03-6 α-(N-benzylidene)-amino-β-hydroxy-β-phenylpropane nitrile 
• 1582302-33-7 C₉H₇FN₂ 
• 100-52-7 benzaldehyde 
• 1582302-34-8 C₉H₇FN₂ 
• 1582302-35-9 C₉H₇N₃O₂ 
• 1582302-36-0 C₉H₇N₃O₂ 
• 1582302-37-1 C₇H₆N₂O 
• 1582302-38-2 C₇H₆N₂S 
• 22483-19-8 [2-Methyl-prop-(E)-ylideneamino]-acetonitrile 
• 1582302-29-1 C₈H₇N₃ 

Relevant academic research and scientific papers

Synthesis of β-prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles

A novel two-step synthesis of multisubstituted β-prolinols has been developed, featuring a [3+2] cycloaddition of azomethine ylides and a programmed reduction triggered by the combination of borane and lithium aluminum hydride (LAH). β-Prolinols are shown to be valuable building blocks for polyheterocycles.

The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of (±)-Isoretronecanol

The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted pyrrolidines. The transformation includes the silver acetate

Silver-catalyzed dynamic systemic resolution of α-iminonitriles in a 1,3-dipolar cycloaddition process

A dynamic azomethine ylide system was established using Sc(OTf)3 and Ag/Taniaphos as catalysts. The system was subsequently kinetically resolved in a tandem 1,3-dipolar cycloaddition process where the silver complex acted as both a reaction catalyst and an external selector, resulting in the formation of an exclusive pyrrolidine product in good yield and enantiopurity. This journal is the Partner Organisations 2014.

Flash vacuum thermolysis generation and a UV-photoelectron spectroscopy study of the N-substituted iminoacetonitriles

Flash vacuum thermolysis of cis and trans 1-benzyl and 1-allyl-2-cyano-3-phenylzetidines (1a and 1b) at 470 °C resulted in the formation of E and Z isomers of N-benzyl and N-allyl iminoacetonitriles 2a and 2b, respectively, beside small amounts of product

The synthesis of alkyl aryl nitriles from N-(1-arylalkylidene)-cyanomethylamines. Part 2. Mechanism

The mechanism of the rearrangement of N-(1-arylalkylidene)cyanomethylamines ArC(=NCH2CN)R 1 to the corresponding nitriles ArCH(CN)R2 (in DMF, at 150°C, with K2CO3) is described. Reaction 1 → 2 was investigated for different types of imine 1, and it was found that with a leaving group other than CN- the reaction does not proceed to yield the nitrile, whereas imines such as PhC(=NCH2CN)H, prepared starting from aldehydes rather than ketones, yield the expected phenylacetonitrile even at temperatures as low as 120°C. Evidence for the mechanism comes from a study of the reactivity of the postulated intermediates: 2-cyano-3-phenylaziridine 4c, and 2,2-diphenyl-2H-azirine 5b. The route involving aziridine 4c is ruled out, since this compound does not react at all under the investigated conditions. The 2H-azirine 5b instead, yields the corresponding diphenylacetonitrile in DMF with K2CO3, at 150°C. The transformation seems to involve an initial deprotonation, followed by an intramolecular ring closure-CN elimination step, which yields the 2H-azirine. The azirine then isomerizes to the nitrile. Additional evidence for the intermediacy of the 2H-azirine, based on 1H NMR monitoring of the reaction 1 → 2, is described. Finally, the results of a simple isotope exchange experiment provide a rationale for the previously observed scrambling of labels, and further confirm the proposed mechanism.

Efficient synthesis of N-alkylformimidoyl cyanides

N-Alkylformimidoyl cyanides (RRCHN=CHCN, 1) were obtained through a very efficient oxidation of N-alkylaminoacetonitriles (RRCHNHCH2CN, 2) by aq. NaOCl. The reaction was run under very mild and simple conditions and afforded products (as E/Z isomer mixtures; E/Z ratio of 70-99%) in short reaction times (30-180 min), and in good to excellent yields (67-97%).