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Хуснутдинов, Р. И.; Shchadneva, N. А.; Baiguzina, A. R.; Lavrentieva, Yu. Yu.; Джемилев, У. М.

doi:10.1023/a:1021668011691

Cited by 25 publications

(39 citation statements)

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“…Using thiophene as an example, it was demonstrated that the reaction is catalyzed not only by VO(acac) 2 but also by iron-and molybdenum compounds. Of the iron and molybdenum compounds examined in the present study (FeCl 3 , FeBr 2 , Fe(OAc) 2 , Fe(acac) 3 , MoO 3 , MoCl 5 , Mo(CO) 6 ), Fe(acac) 3 and Mo(CO) 6 proved to be most efficient in this reaction.…”

Section: Methodsmentioning

confidence: 66%

“…However, the reaction starting from 2-methylthiophene 3 and the CCl 4 -CD 3 -VO(acac) 2 system afforded 2-methyl-5-trideuteriomethylthiophenecarboxylate, 4, i.e., the reaction product contained deuterium exclusively in the methoxy group, which argues against the above assumption. …”

Section: Methodsmentioning

confidence: 98%

“…In the present study, we used the CCl 4 -CH 3 OH-VO(acac) 2 system for oxidation of thiophene and its derivatives. Unexpectedly, the reaction of thiophene 1 with this system gave, along with CHCl 3 and HCl, methyl 2-thiophenecarboxylate 2 as the major product.…”

Section: Methodsmentioning

confidence: 99%

“…It should be noted that the reaction requires drastic conditions and occurs at 130, 140, and 175 o C in the presence of Mo(CO) 6 , Fe(acac) 3 , and VO(acac) 2 , respectively. Because of high temperature, the reaction was carried out in a sealed tube or a stainless-steel micro-autoclave.…”

Section: Methodsmentioning

confidence: 99%

“…Under typical conditions (175 o C, 5 h), the reaction in the presence of VO(acac) 2 at concentrations of 0.1, 0.2, and 1.0 mol. % with respect to thiophene afforded product 2 in 25, 31, and 45% yield, respectively.…”

Section: Methodsmentioning

confidence: 99%

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New method for the synthesis of 2-thiophenecarboxylic acids in the presence of V-, Fe-, or Mo-containing catalysts

Хуснутдинов¹,

Shchadneva²,

Bayguzina³

et al. 2004

Arkivoc

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2-Thiophenecarboxylic acid and its derivatives were synthesized by the reaction of thiophenes with the CCl 4 -CH 3 OH-catalyst system in total yields of 44-85%. The probable scheme of the reaction involves successive oxidation of methanol with tetrachloromethane to methyl hypochlorite and formaldehyde. Under the action of the latter, thiophene undergoes oxymethylation, giving rise to 2-oxymethylthiophene, which is oxidized with CH 3 OCl to 2-thiophenecarboxylic acid. In the presence of an excess of CH 3 OH, the latter is subjected to esterification. It was found that Fe(acac) 3 , VO(acac) 2 , and Mo(CO) 6 are the catalysts of choice for this reaction.Keywords: Catalysis, iron, vanadium and molybdenum compounds, methyl hypochlorite, thiophene, 2-thiophenecarboxylic acid, oxidation Results and DiscussionEarlier, we reported 1,2 that the manganese-and vanadium-complexes [Mn(acac) 3 and VO(acac) 2 ] catalyze the oxidation of alcohols (ROH) under the action of CCl 4 giving rise to alkyl hypochlorites (ROCl). Subsequent transformations of ROCl depend on the structure of the radical R. Lower primary alcohols are most readily oxidized. For example, oxidation of methanol with tetrachloromethane in the presence of Mn(acac) 3 affords predominantly methyl formate along with small amounts of formaldehyde. Hydrochloric acid and trace amounts of CH 2 Cl 2 , CH 3 OCH 3 , and water were also found in the reaction mixture. In the course of the reaction, CCl 4 is reduced to CHCl 3 .

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Section: Methodsmentioning

confidence: 66%

Section: Methodsmentioning

confidence: 98%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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