50979-38-9

Upstream product

• 1070-92-4 bis(ethylsulfonyl)methane 
• 100-34-5 benzene diazonium chloride 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 2166-14-5 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester 
• 670-54-2 ethenetetracarbonitrile 
• 764-42-1 1,2-Dicyanoethylene 
• 140-22-7 1,5-diphenylcarbazide 
• 1087-09-8 1,4-diphenyl-but-2-yne-1,4-dione 
• 1768-59-8 1,4-diphenylthiosemicarbazide 

Downstream Products

• 100-63-0 phenylhydrazine 
• 60078-01-5 dicyano-α-(1,3-diphenyltetrazol-5-ylio)methylide 
• 104329-25-1 cyanoethoxycarbonyl-α-(1,3-diphenyltetrazol-5-ylio)methylide 
• 64-10-8 phenyl carbamate 
• 62-53-3 aniline 

Relevant academic research and scientific papers

5-Nitroso-1,3-diphenyltetrazolium salt as a mediator for the oxidation of alcohols

We describe the synthesis of a mesoion-derived nitroso compound, 5-nitroso-1,3-diphenyltetrazolium tetrafluoroborate (1), and its application in the oxidation of alcohols. The structure of 1 was fully characterized by X-ray analysis, showing that it exists as a monomer in the solid state. In the cyclic voltammetric analysis of 1, a reversible redox peak was observed at 0.43 V (vs. Ag/Ag+ in MeCN) under acidic conditions. It was subsequently shown that the nitrosotetrazolium salt 1 is capable of stoichiometrically oxidizing alcohols to the corresponding carbonyl compounds effectively. This nitroso heterocycle and its reduced form, i.e., the corresponding mesoionic hydroxyamide, participate in a redox cycle involving the catalytic oxidation of alcohols by the aid of HNO3 under mild conditions.

Synthesis method of 1, 3-diaryl substituted tetrazolone inner salt

The invention provides a method for synthesizing 1, 3-diaryl substituted tetrazolone inner salt, which comprises the following steps of: a, reacting a diaryl semicarbazide reagent serving as a reaction raw material in a reaction solvent under the action of a catalyst and alkali to obtain the 1, 3-diaryl substituted tetrazolone inner salt, mixing 0.5 mmol of diarylaminourea with 10 mol% of palladium acetate serving as a catalyst, adding 1.0 mmol of potassium carbonate serving as alkali, putting the mixed solution into a solvent, controlling the reaction temperature to be 70-100 DEG C, and magnetically stirring for 2-4 hours; b, in the reaction process, TLC is used for monitoring the complete reaction, after the reaction is finished, the temperature is reduced to the room temperature, afterthe reaction is finished, a proper amount of water is added for quenching reaction treatment, then a proper amount of dichloromethane is added for extraction, anhydrous sodium sulfate is added for drying, the solvent is subjected to reduced-pressure spin-drying, and then pure 1, 3-diaryl substituted tetrazolone inner salt is obtained through column chromatography separation.

Reactions between 5-Nitroso-1,3-diphenyltetrazolium salts and electron-rich arenes, amines, thiophenol, sulfoxides, and thioanisole

A series of reactions between 5-nitroso-1,3-diphenyltetrazo-lium tetrafluoroborate and methoxybenzenes, amines, thiols, sulfoxides, and sulfides, most of which are generally accepted as being inert to nitroso groups, is reported here. The tetrazolium-activated nitroso functionality is capable of oxidizing the aforementioned substrates to give the corresponding oxidized products, and the nitroso tetrazolium itself is transformed into the corresponding amide or hydroxyamide, depending on the nature of the reaction partners. In the case of thioanisole, an addition product was obtained.

Mesoionic carbenes: Reactions of 1, 3-diphenyltetrazol-5-ylidene with electron-deficient alkenes, and synthesis and catalytic activities of the (tetrazol-5-ylidene)rhodium(I) complexes

The reactions of 1, 3-diphenyltetrazol-5-ylidene, a rare example of mesoionic carbenes, with electron- deficient unsaturated compounds were studied. The carbene reacted with dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylate to give a 5-tetrazoliomethylide, together with hydrazine derivatives. The reaction with tetracyanoethylene gave another methylide in low yield. On the contrary, the reactions with weaker electrophiles, such as 3, 6-diphenyl-1, 2, 4, 5-tetrazine, fumalonitrile, N-phenylmaleimide, and dimethyl acetylenedicarboxylate, did not give any coupling products, but gave phenylated products and/or Michael addition products via the degradation of the 1, 3-diphenyltetrazole ring. Novel mesoionic mono- and bis(carbene)-rhodium(I) complexes were synthesized and the structures were characterized by X-ray crystallography. Their catalytic activities for the decarbonylative addition reaction of benzoyl chloride to ethynylbenzene were investigated.

Reaction cascades initiated by nucleophilic attack of heteropentalene mesomeric betaine and nitrogen-rich mesoionic tetrazolium-5-amides on electron-deficient unsaturated compounds. Synthesis of novel heterocyclic systems.

The reactions of heteropentalene mesomeric betaine 1 and nitrogen-rich mesoionic tetrazolium-5-amides 4, 11 and 16-18 with electron-deficient unsaturated compounds have been studied. Novel heterocyclic systems, tetrazolo[4,5-a][1,7]benzodiazonine inner sa

The photochemical reactions of nitrogen-rich mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds

Photochemical reactions of azo and triazo derivatives of mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds were studied. The reaction paths were found to depend markedly on the types of substrate, substituent and reaction solvent giving diverse products. Upon irradiation of the 1,1′3,3′-tetraphenylazoditetrazolium salt 1, the addition of hydrogen and acetone to the N=N bond was observed in methanol and acetone, respectively, whereas the bond was cleaved in diethyl ketone to give the 5-aminotetrazolium salt 10. The corresponding radical cation 11 also gave the reduction product in methanol. On the other hand, the 1,3-diphenyl-5-(phenylazo)tetrazolium salt 12 underwent nitrogen evolution giving the 1,3-diphenyltetrazolium salt 13 via the corresponding tetrazolium radical. Triazene derivatives 14 and 17 underwent an N-N bond cleavage to give tetrazolio-5-amide 4. The mesoionic triazene compounds bearing a tosyl 18 or cyano group 19 gave products 20 and 23. Triphenylphosphinotriazene 24 liberated nitrogen to give phosphinoimide 25 and its hydrolysis product 10. Tetrazolylamide 26 lost a phenyldiazonium group from the 1,3-diphenyltetrazolium ring to give the guanidine derivative 27.

Photochemistry of mesoionic compounds. Photochemical conversion of 5-azido-1,3-diaryltetrazolium salts to novel tricyclic mesoions with a tetrazolo[1,5-a]benzimidazole skeleton

A new type of tetrazolium-5-amide mesoions 2 with a tricyclic tetrazolo[1,5-a]benzimidazole skeleton has been synthesized via photolysis of 5-azido-1,3-diaryltetrazolium salts 1.

Nitrogen-rich mesoionic compounds from 1,3-diaryl-5-chlorotetrazolium salts and nitrogen nucleophiles - Synthesis and properties of 1,3-diaryl-5-azidotetrazolium salts

Nitrogen-rich mesoions have been synthesized by the reaction of the 5-chloro-1,3-diaryltetrazolium salt 1 with various nitrogen nucleophiles. The reactions with aqueous ammonia and hydroxylamine gave tripolar mesoionic amide 2 and mesoionic hydroxylamide 4, respectively. N-Substituted and N,N-disubstituted hydrazines yielded the corresponding hydrazides 5, whereas N,N-diphenylhydrazine gave the rearranged product 6. The reaction with sodium azide gave 5-azidotetrazolium salt 8. The azido group of 8 was reduced to give aminotetrazolium salt 9, deprotonation of which yielded the corresponding conjugate base 3. Hard nucleophiles attacked the tetrazolium carbon atom of 8 to give substitution products, whereas soft nucleophiles added the terminal nitrogen atom of the azido group to give addition products. Azido-tetrazolium salt 8 reacted further with sodium azide to give a high yield of the tetrazol derivative 11, together with a small amount of triazene 17. The intermediacy of mesoionic carbene 19 is postulated.