93961-30-9

Upstream product

• 22812-58-4 methyl 2-diazo-2-(4-nitrophenyl)acetate 
• 75-05-8 acetonitrile 
• 67-56-1 methanol 

Downstream Products

• 105495-02-1 7-Hydroxy-4-methyl-6-(4-nitro-phenyl)-pyrrolo[3,4-c]pyridine-1,3-dione 
• 105494-96-0 (1S,6R,7R)-1-Methoxy-7-methyl-9-(4-nitro-phenyl)-10-oxa-4,8-diaza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 105494-96-0 (1S,2R,6S,7R)-1-Methoxy-7-methyl-9-(4-nitro-phenyl)-10-oxa-4,8-diaza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 105494-93-7 (1S,2R,6S,7R)-1-Methoxy-4,7-dimethyl-9-(4-nitro-phenyl)-10-oxa-4,8-diaza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 105494-93-7 (1S,2S,6R,7R)-1-Methoxy-4,7-dimethyl-9-(4-nitro-phenyl)-10-oxa-4,8-diaza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 105494-99-3 7-Hydroxy-2,4-dimethyl-6-(4-nitro-phenyl)-pyrrolo[3,4-c]pyridine-1,3-dione 
• 105495-00-9 2-Ethyl-7-hydroxy-4-methyl-6-(4-nitro-phenyl)-pyrrolo[3,4-c]pyridine-1,3-dione 
• 135673-08-4 5-Methyl-3-(4-nitro-phenyl)-3H-[1,2,4]triazole-1,2,3-tricarboxylic acid 1,2-diethyl ester 3-methyl ester 
• 109988-44-5 methyl 3,3,4,4-tetracyano-4,5-dihydro-2-methyl-5-(p-nitrophenyl)-3H-pyrrole-5-carboxylate 
• 105495-05-4 2-Methoxy-5-methyl-furan-3,4-dicarboxylic acid dimethyl ester 
• 105495-06-5 1-Methoxy-4-methyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3,5,6-tetracarboxylic acid tetramethyl ester 
• 619-72-7 4-nitrobenzonitrile 
• 135673-02-8 5-methoxycarbonyl-3-methyl-5-(p-nitrophenyl)-2-phenyl-2,5-dihydro-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Mechanistic studies of direct and sensitized photolysis of methyl (4-nitrophenyl)diazoacetate in the presence of an electron-donating amine: Photochemical generation of the diazoalkane radical anion

The direct and perylene-sensitized photolysis of methyl (4-nitrophenyl)diazoacetate (1) in the presence of an electron-donating amine was investigated by the characterization of reaction products and by the direct observation of reactive species using a laser flash photolysis technique. In the direct photolysis of 1 in the presence of N,N,N′,N′-tetramethyl-p-phenylenediamine (TMPD), electron transfer from TMPD occurs and the photoproducts are obtained through an intermediate other than the carbene 3, which we suppose to be the carbene radical anion 3-·. In the perylene-sensitized photolysis of 1 in the presence of an amine having a large electron-donating ability such as N,N-dimethylaniline and TMPD, the radical anion of 1 can be generated by perylene-mediated electron transfer from the amine to 1. The resulting 1-· appears to undergo extrusion of dinitrogen to give 3-· smoothly, the behavior of which is dependent on the amine employed as an additive. The product studies revealed that 3-· reacts readily with O2 to give the ketoester 5 or abstracts hydrogen atoms to give the ester 7, which is not inconsistent with the theoretical prediction that 3-· has a σ radical character in its electronic structure.

Photoreaction of methyl (p-nitrophenyl)diazoacetate in the presence of an electron-donating amine: Evidence for intermediacy of the carbene radical anion

The product distribution in the photolysis of methyl (p-nitrophenyl)diazoacetate in MeCN-MeOH (9:1) was dramatically changed by the addition of an electron-donating amine, where the formation of the products derived from the carbene was quenched completely. On the basis of the direct observation of transient species and the dependence of the products on amine concentration, the reaction scheme involving a single electron transfer to afford the carbene radical anion is proposed.

ACID-CATALYZED DECOMPOSITION OF DIAZO CARBONYL COMPOUNDS. II. SYNTHESIS OF 2- OR 5-HETEROATOM-SUBSTITUTED OXAZOLES.

The BF//3-catalyzed decomposition of m- and p-substituted alpha -diazoacetophenones in excess of methyl thiocyanate and ethyl thiocyanate gave the corresponding 2-methylthio-, and 2-ethylthio-5-aryloxazoles, respectively in good yields along with s-alkyl-