Benzoylation of deactivated compounds of the thiophene and furan series with phenyldichlorocarbenium tetrachloroaluminate

Беленький, Л. И.; Gromova, G. P.; Колотаев, А. В.; Krayushkin, М. М.

doi:10.1007/bf02256861

Cited by 7 publications

(2 citation statements)

References 10 publications

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“…Particularly, we have shown 5 that in the presence of aluminum chloride, benzotrichloride reacts with 2-acetylthiophene selectively and at lower temperature than benzoyl chloride to give diketone 2a in a much higher yield (50% 5 instead of 13% 4 ).…”

Section: Resultsmentioning

confidence: 91%

Aroylation of 2- and 3-acetylthiophenes using benzoyl chloride, benzotrichloride, and their substituted derivatives

Беленький¹,

Gromova²,

Колотаев³

et al. 2002

Arkivoc

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Dedicated to Professor Mikhail G. Voronkov on the occasion of his 80th birthday (received 01 Jun 01; accepted 08 Jan 02; published on the web 16 Jan 02) Abstract Aryldichlorocarbenium tetrachloroaluminates are shown to be preferable reagents for the aroylation of 2-acetylthiophene, while the usual ArCOCl·AlCl 3 complexes give better results in aroylation of 3-acetylthiophene. Scope and limitations of both aroylation procedures are discussed.

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Section: Resultsmentioning

confidence: 91%

Aroylation of 2- and 3-acetylthiophenes using benzoyl chloride, benzotrichloride, and their substituted derivatives

Беленький¹,

Gromova²,

Колотаев³

et al. 2002

Arkivoc

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“…However, the synthesis of trichloromethylarenes and trichloromethylhetarenes only goes satisfactorily in the presence of a substituent even though it is at one of the positions adjacent to the point of entry of the CCl 3 group. At the same time aryldichloromethyl cations or, more accurately, the ion pairs ArCCl 2 + AlCl 4 − are substantially more active electrophilic agents than ArCOCl·AlCl 3 complexes and have been used in particular for the introduction of aroyl groups into deactivated derivatives of thiophene and furan -ketones and esters [112,113].…”

Section: Investigations Of Some Compounds Of the Benzene Series And Tmentioning

confidence: 99%

Development of quantum-chemical investigations of heterocycles at the Institute of Organic Chemistry, Russian Academy of Sciences (review)

Беленький

Чувылкин

2011

Chem Heterocycl Comp

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of attack by electrophile (position selectivity), relative stability of onium ions, stable thiophenium ions, their transformations.This review is dedicated to the memory of the distinguished organic chemist, one of the "founding fathers" of the journal "Chemistry of Heterocyclic Compounds", Professor, Doctor of chemical sciences, eminent man of science and technology of the RSFSR Ya. L. Gol'dfarb. As a scientist Prof. Gol'dfarb invariably showed a keen interest in all that was new and progressive in science, and the last 30 years of Yakov Lazarevich's life, when instrumental methods and theoretical concepts were being vigorously developed, were exceptionally prolific. It is no wonder that even in 1970-1971 Ya. L. Gol'dfarb became the initiator of the use of quantum-chemical methods in work at the synthesis laboratories of the N. D. Zelinsky Institute of Organic Chemistry. The possibilities of quantum-chemical methods have certainly increased substantially over the last 40 years, but the pioneering work still retains its significance in that appropriate models were carefully selected and the results of the calculations were always matched with the experimental data.Typically, the quantum-chemical calculations were no way to "dress up" the work carried out in the laboratory but were directed toward a meaningful study of the reactivity of heteroaromatic compounds, and to this day investigations are conducted with close collaboration between specialists in organic synthesis and specialists in the field of quantum chemistry. It is no coincidence that even in 1972 experimental data existing at that time on the reactivity and structure of compounds of the thiophene and furan series carrying electronaccepting substituents were being analyzed in detail on the basis of the results of quantum-chemical calculations performed at the Institute of Organic Chemistry, USSR Academy of Sciences [1], while in1977 the _______ * In happy memory of Yakov Lazarevich Gol'dfarb.

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ChemInform Abstract: Benzoylation of Deactivated Compounds of the Thiophene and Furan Series with Phenyldichlorocarbenium Tetrachloroaluminate.

et al. 2000

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Benzoylation of deactivated compounds of the thiophene and furan series with phenyldichlorocarbenium tetrachloroaluminate

Abstract: The reactions of henzotrichloride with methyl and ethyl esters and nitriles ~f lthiophene,

Cited by 7 publications

References 10 publications

Aroylation of 2- and 3-acetylthiophenes using benzoyl chloride, benzotrichloride, and their substituted derivatives

Aroylation of 2- and 3-acetylthiophenes using benzoyl chloride, benzotrichloride, and their substituted derivatives

Development of quantum-chemical investigations of heterocycles at the Institute of Organic Chemistry, Russian Academy of Sciences (review)

ChemInform Abstract: Benzoylation of Deactivated Compounds of the Thiophene and Furan Series with Phenyldichlorocarbenium Tetrachloroaluminate.

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