117873-01-5

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 36602-08-1 (N-methylanilino)acetonitrile 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 132431-15-3 2-(N-methylanilino)-2-phenylsulfanylacetonitrile 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 117873-09-3 10-Methyl-9-oxo-2-phenyl-9,10-dihydro-acridine-1-carboxylic acid ethyl ester 
• 157671-32-4 (2E,4E)-2-(N-methyl-4-bromoanilino)-5-phenyl-2,4-pentadienenitrile 
• 14371-10-9 (E)-3-phenylpropenal 
• 99839-93-7 N-methyl-N-phenyl-carbamoyl cyanide 
• 117873-05-9 4-(Methyl-phenyl-amino)-7-phenyl-isobenzofuran-1,3-dione 

Relevant academic research and scientific papers

2-(N-Methylanilino)-2-phenylsulfanylacetonitrile, A Reagent Tested for Electrophilic, Nucleophilic, and Radical Reactions

2-(N-Methylanilino)-2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide.Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates.Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by CuI or Lewis acids to give varied α-amino nitriles.The 4-oxo-2-aminonitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung.When 1 was treated with tributylstannane, the corresponding amino nitrile α-radical was formed and the self-coupling product was isolated.

Solution and Solid-State Photochemistry of 2-Anilino-5-phenyl-2,4-pentadienenitriles

2-(N-Methylanilino)-5-phenyl-2,4-pentadienenitrile (3) undergoes either isomerization or oxidative cleavage at the 2,3-double bond upon irradiation in solution, whereas it dimerizes in a regiospecific manner to give the cycloaddition product 12 upon irradiation in the solid state.From the fluorescence spectra and semiempirical calculations, the excited state of 3 is proposed to be a twist intramolecular charge transfer species.The X-ray analysis indicates that molecules of 3b orient appropriately with a reasonable distance for the cycloaddition in the solid state.The distance between C2 and C3' is 525 pm, the longest distance known in solid-state cycloadditions. 2-(N-Methyl-p-bromoanilino)-5-phenyl-2,4-pentadienenitrile (4) shows behavior similar to that of 3 in the solution and solid-state photochemistry, whereas analogs 7-10 having nitro substituents on the 5-phenyl rings do not dimerize upon irradiation in the solid state.Semiempirical calculation of the electronic structures is used to interprete the discrepancy of reactivity.

Use of α-Anilino Dienenitriles as Nucleophiles in Cycloadditions

The α-anilino dienenitriles 1-5 were prepared.The dienes 1-3 reacted with dichlorocarbene and electrophiles containing electron-deficient double bonds such as maleic anhydride, benzoquinone, dimethyl acetylenedicarboxylate, tetracyanoethylene, and chlorosulphonyl isocyanate.The diarylmethylamines 8-10, generated by cycloaddition of α-anilino dienenitriles and maleic anhydride, were successfully transformed into acridones 15-17.Intramolecular cyclization of trienes 4 and 5 yielded the carbazoles and dihydro derivatives, accompanied by formation of 2-cyano-1-methylindole.