Heteroaromatic carbenes (review)

Shvaika, O. P.; Коротких, Н. И.; Aslanov, A. F.

doi:10.1007/bf00531470

Cited by 12 publications

(16 citation statements)

References 87 publications

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“…Current methods for the preparation of іmіdazol-2-ylіdenes involve the deprotonation of meso-unsubstituted іmіdazolіum salts under the action of anhydrous and unprotic bases (metal hydrides, alkoxides, hexamethyldisilazanides, diisopropylamides, etc.). Using this approach Wanzlick et al 7 generated carbenes of the heterocyclic series in situ. However, Arduengo et al provided the first example of a stable crystalline carbene 1,3-dі-(1-adamantyl)іmіdazol-2-ylidene 1D2 (R = 1-Ad) (Scheme 1).…”

Section: Synthesis Of Carbenes Of the Imidazole And Triazole Series Amentioning

confidence: 99%

“…7,9,168,198 As such, these reagents can act as alcohols, thiols or amines. However, such insertion products are generally labile and upon heating transform back into the original carbenes.…”

Section: х-н Insertion Reactions 421 Insertions Into Polar х-н Bondsmentioning

confidence: 99%

“…The preparation of other types of individual carbenes took longer to materialise. 6,7 However, today a large number of compounds have been isolated; these are predominantly heterocyclic species and include heteroaromatic carbenes, phosphanylsilylcarbenes, aminoalkyl-and diamino-carbenes of cyclic and acyclic series, borazino-and borazolo-carbenes, etc. [8][9][10][11][12][13][14][15][16][17][18][19][20] One of the major focuses of carbene applications has been the catalysis of organic reactions.…”

Section: Introductionmentioning

confidence: 99%

“…The results of such reactions are often comparable to those of free carbenes. 7 Structures are numbered in this review according to the Scheme in which they first appear, in order to avoid a cumbersome sequence running into the 500s. We hope that this will be found convenient.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of heteroaromatic carbenes of the imidazole and triazole series and their fused analogues

Коротких¹,

Cowley²,

Clyburne³

et al. 2017

Arkivoc

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Section: Synthesis Of Carbenes Of the Imidazole And Triazole Series Amentioning

confidence: 99%

Section: х-н Insertion Reactions 421 Insertions Into Polar х-н Bondsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and properties of heteroaromatic carbenes of the imidazole and triazole series and their fused analogues

Коротких¹,

Cowley²,

Clyburne³

et al. 2017

Arkivoc

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“…Reactions of this type were investigated originally by Wanzlick et al [1][2][3] and have been reported subsequently by other research groups. [4][5] Furthermore, the corresponding reactions with acetonitrile, dimethylsulfone and acetylenes have been carried out with stable carbenes such as 1,3-dialkylbenzimidazol-2-ylidenes, 1-alkyl-3,4-diaryl-1,2,4-triazol-5-ylidenes [6][7][8][9] and 1,3-dimesitylimidazolin-2-ylidene However, thus far the analogous transformations of highly basic acyclic tetraalkyldiaminocarbenes have not been explored. Such reactions are of considerable potential interest as a source of acyclic diaminomethane derivatives.…”

Section: Introductionmentioning

confidence: 99%

A base induced transformation of a 1,3-dimethyl-1,3-di(1-adamantyl)formamidinium salt into β-[methyl-(1-adamantyl)amino]acrylonitriles in aliphatic nitriles

Knishevitsky

Коротких

Cowley³

et al. 2012

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Structure and characteristics of the ionic forms of heteroarenium salts in organic solvents (review)

Shvaika

Kovach

2009

Chem Heterocycl Comp

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The results of investigations into the formation of the various ionic forms of heteroarenium salts, their characteristics, and their reactivity are summarized. Salts containing (4n+2)π-electron aromatic cations (n = 0-3), including chalcogenopyrylium (O, S, Se), azinium, benzo-and dibenzoazinium, and chalcogenoazolium (O, S, Se, NR) ions are examined. In this system of compounds the relationships between the structure and the macroscopic characteristics of the heteroarenium salts (ionization constants, association/dissociation constants, distances of closest interionic approach) and the effect of the nature of the ionic forms in the solutions on their reactivity in heterolytic reactions are analyzed.Salt forms and in particular heteroarenium salts occupy an extremely important position in the chemistry of heterocyclic compounds, being of interest both in structural respects and in their high reactivity in nucleophilic reactions, recyclization reactions [1-3], and more recently at the applied level as ionic liquids [4]. It is on the basis of heteroarenium salts that the modern chemistry of stable carbenes -the organic chemistry of the divalent carbon atom -has developed [5][6][7][8][9].In spite of numerous investigations into the structure of the salts, carried out by various physicochemical methods (spectral, polarographic, X-ray crystallographic, etc.) direct information about their properties as salts, i.e., their capacity for dissociation/association and the formation of various ionic forms (free ions, various ionic associates -ion pairs and ion triplets), has remained almost in the dark. Among the characteristics directly describing the state of heteroarenium salts in solutions the most important are clearly the thermodynamic characteristics (which can be regarded as macroscopic in contrast to the microscopic characteristics relating, for example, to the spectral characteristics) -the ionic association (K a )/dissociation (K d ) constants, the distance of closest approach of the ions, and theories about the dependence of these quantities on the structure of the salts. Information on the ionic association of heteroarenium salts is of considerable interest for assessing their reactivity. It is also important for understanding the processes that give rise to the effectiveness of organic electrolytes containing heteroaromatic cations in physical systems (e.g., as luminophores [10]).

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Heteroaromatic carbenes (review)

Cited by 12 publications

References 87 publications

Synthesis and properties of heteroaromatic carbenes of the imidazole and triazole series and their fused analogues

Synthesis and properties of heteroaromatic carbenes of the imidazole and triazole series and their fused analogues

A base induced transformation of a 1,3-dimethyl-1,3-di(1-adamantyl)formamidinium salt into β-[methyl-(1-adamantyl)amino]acrylonitriles in aliphatic nitriles

Structure and characteristics of the ionic forms of heteroarenium salts in organic solvents (review)

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