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Journal articles on the topic 'Carbanions'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Grossert, J. Stuart, Jeffrey Hoyle, T. Stanley Cameron, Stephen P. Roe та Beverly R. Vincent. "The structures of some sulphur-stabilized carbanions and stereoelectronic requirements for the formation of α-sulphonyl carbanions". Canadian Journal of Chemistry 65, № 6 (1987): 1407–15. http://dx.doi.org/10.1139/v87-238.

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Relatively few structure determinations of α-sulphonyl stabilized carbanions have been reported. The salient features of these are summarized and discussed in the light of the X-ray crystal structures of the potassium salt from bis(methylsulfonyl)-3-(2,6-dimethoxypyridyl)sulfonylmethane (5), the carbon acid bis(methylsulphonyl-4-(1,3-dimethoxyphenyl)sulphonylmethane (6), the triethylammonium salt of 2-methylsulphonyl-2-phenylthio-1-(3-pyridyl)-1-ethanone (7), the carbon acid 2-methyl-sulphonyl-2-phenylthio-1-phenylethanone (8), and its triethylammonium salt (9). Results of these structure dete

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2

Toman, Jaromír, Jaromír Mindl, Antonín Lyčka, Jiří Klicnar, Ivana Srovnalová, and Miloš Koníček. "Structure of Reaction Products of Some Substituted Quinoxaline N-Oxides with Carbanions." Collection of Czechoslovak Chemical Communications 59, no. 11 (1994): 2493–500. http://dx.doi.org/10.1135/cccc19942493.

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1,2,3-Triazolo[1,5-a]- (II) and 1,2,4-triazolo[4,3-a]quinoxaline 5-oxide (III) react with the carbanions of β-diketones and β-keto esters to give enaminones in the same way as their tetrazolo analogue. The difference in mechanism of reactions of these N-oxides with carbanions of 3-alkylpentane-2,4-dione and ethyl methyl acetoacetate giving aziridinopolyazoloquinoxalines and ethyl 2-(polyazoloquinoxalin-4-yl)propanoates, respectively, is discussed. It was shown that the reaction with carbanion including the aziridine ring closure proceeds with 3,4-dihydro-3-oxoquinoxaline-1-oxide as well.

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3

Fischer, Alfred, George N. Henderson, and S. Sankararaman. "Preparation of and addition of carbanions to 6-methyl-6-nitrocyclohexa-2,4-dienones." Canadian Journal of Chemistry 67, no. 7 (1989): 1244–46. http://dx.doi.org/10.1139/v89-189.

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Nitration of 2-methylphenols with nitric acid and trifluoroacetic anhydride in ether at −78 °C gives 6-methyl-6-nitrocyclo-hexa-2,4-dienones that can be isolated. Carbanions add to 5,6-dimethyl-6-nitrocyclohexa-2,4-dienone to give the 5-substituted 2,3-dimethyl-2-nitrocyclohex-3-enone anion, which, with additional carbanion, gives the 5-substituted 2,3-dimethylphenoxide anion by elimination of nitrous acid. Keywords: nitration, dienone, addition, carbanion, nucleophilic.

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4

Katritzky, Alan R., and Ming Qi. "Michael Additions of Benzotriazole-Stabilized Carbanions. A Review." Collection of Czechoslovak Chemical Communications 63, no. 5 (1998): 599–613. http://dx.doi.org/10.1135/cccc19980599.

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The 1,4-addition of benzotriazole-stabilized carbanions to Michael acceptors is reviewed. The selectivity between 1,4- and 1,2-addition depends significantly on the electronic effect of the carbanion (usually lithium is the counterion), the type of the Michael acceptor, and steric effects. Steric hindrance of the benzotriazolyl group probably enhances the regioselectivity. Normally, 1,4-additions to α,β-unsaturated ketone or ester are observed for carbanions stabilized by a benzotriazolyl group and an electron-withdrawing group (e.g. aryl, vinyl, carbonyl). For α,β-unsaturated aldehydes as Mic

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5

Kumagai, Yuta, Takashi Naoe, Keisuke Nishikawa, Kazuyuki Osaka, Toshio Morita, and Yasuharu Yoshimi. "Formation of Carbanions from Carboxylate Ions Bearing Electron-Withdrawing Groups via Photoinduced Decarboxylation: Addition of Generated Carbanions to Benzaldehyde." Australian Journal of Chemistry 68, no. 11 (2015): 1668. http://dx.doi.org/10.1071/ch15115.

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The photoinduced decarboxylation of carboxylate ions bearing electron-withdrawing groups using biphenyl and 1,4-dicyanonaphthalene leads to the efficient generation of carbanions under mild conditions. The efficiency of the carbanion generation is strongly dependent on the single-electron transfer from the photogenerated radical anion of the electron-acceptor to the radical. In particular, the cyanomethyl anion formed using this photochemical method can be added to benzaldehydes to give the corresponding adducts.

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6

Zorin, А. V., A. T. Zaynasheva та V. V. Zorin. "Oxidative heterocoupling of lithium 2-methylpropanoate α-carbanion and secondary α-carbanions of lithium acylates". Журнал общей химии 94, № 4 (2024): 503–10. http://dx.doi.org/10.31857/s0044460x24040049.

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When the α-carbanion of 2-methylpropanoate (A) reacts with the α-carbanions of lithium butanoate, pentanoate, hexanoate, heptanoate and phenylacetate (B) in the presence of 1,2-dibromoethane, a mixture of oxidative homocoupling (A-A, B-B) products [2,2,3,3-tetramethyl- and 2,3-diethyl- (or 2,3-dipropyl-, 2,3-dibutyl-, 2,3-dipentyl-, 2,3-diphenyl)succinic acids] and heterocouplings (A-B) products [2,2-dimethyl-3-ethyl- (or 2,2-dimethyl-3-propyl-, 2,2-dimethyl-3-butyl-, 2,2-dimethyl-3 -pentyl-, 2,2-dimethyl-3-phenyl)succinic acids] is formed with a total yield of 84–98%. The effect of the nature

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7

Zorin, Alexander V., Aliya R. Chanysheva, Anastasia O. Lenkova та Vladimir V. Zorin. "INTERACTION OF α-CARBANIONS OF LITHIUM ACYLATES WITH 1,2-DIBROMOALKANES". IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, № 4 (2020): 12–16. http://dx.doi.org/10.6060/ivkkt.20206304.6150.

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We have studied the interaction of α-carbanions of lithium acylates with 1,2-dibromoalkanes with different length of the carbon chain in order to establish the direction of the reaction. Interaction of α-carbanions of lithium acylates obtained by metallation of acetic, butyric and isobutyric acids with lithium diisopropylamide and 1,2-dibromoalkanes (1,2-dibromohexane, 1,2-dibromoheptane or 1,2-dibromononane) with a molar ratio of reactants equal to 1: 2: 1 in argon atmosphere in tetrahydrofuran under normal conditions (20-25 °C) for 2 h leads to the products of the oxidative coupling of enola

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8

Han, Ling-Li, and Tao Liu. "Theoretical study on the nucleophilic fluoroalkylation of propylene oxide with fluorinated sulfones." Journal of the Serbian Chemical Society 78, no. 4 (2013): 483–94. http://dx.doi.org/10.2298/jsc120831097h.

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The path of nucleophilic fluoroalkylation reaction of propylene oxide with PhSO2CYF- (Y=F,H, and PhSO2, respectively) in gas phase and in Et2O solvent were studied theoretically. The nucleophilic fluoroalkylation of propylene oxide with fluorinated carbanions was probed by the reactivity comparison between (benzenesulfonyl)monofluoromethyl anion (PhSO2CHF-), (benzenesulfonyl) difluoromethyl anion (PhSO2CF2-), and bis(benzenesul-fonyl) monofluoromethyl anion ((PhSO2)2CF-). The nucleophilicity reactivity order of PhSO2CYF- (Y = F, H, and PhSO2) is [(PhSO2)2CF-] > PhSO2CHF- > PhSO2CF2-, whi

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9

Menn, Jean-Christophe Le, Jean Sarrazin, and André Tallec. "Carbanions phosphonate préparés par voie électrochimique: formation et réactivité vis-à-vis d'un aldéhyde." Canadian Journal of Chemistry 67, no. 8 (1989): 1332–43. http://dx.doi.org/10.1139/v89-205.

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Reactivity towards p-methoxybenzaldehyde (ArCHO) of electrochemically generated phosphonate carbanions has been investigated. Electrolyses were carried out at a mercury cathode in DMF and two routes to the desired carbanion have been compared: (i) Deprotonation of phosphonates of general formula (EtO)2P(O)CHYW (Y = W = Cl; Y = H, W = Cl; Y = Cl, W = CO2Et; Y = H, W = CO2Et; Y = CH3, W = CO2Et; Y = Cl, W = CH3), by the bases resulting from the electroreduction of azobenzene; addition of the carbanion formed onto the carbonyl group takes place and leads to the adduct (EtO)2P(O)CYW(Ar)O−. (ii) Tw

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10

Asghar, Basim H. M., Michael R. Crampton та Chukwuemeka Isanbor. "Carbanion reactivity — σ-adduct formation and elimination in the reactions of the carbanion from bis(phenylsulfonyl)methane with 4-nitrobenzofurazan derivatives". Canadian Journal of Chemistry 86, № 3 (2008): 225–29. http://dx.doi.org/10.1139/v08-010.

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1H NMR studies in [2H6]-DMSO show that the carbanion 4 from bis(phenylsulfonyl)methane reacts with 4,6-dinitrobenzofuroxan to yield a σ-adduct that undergoes base-catalysed elimination to yield an alkene derivative. Rate constants, measured spectrophotometrically, are reported for the corresponding reactions in methanol of 4 with 4-nitrobenzofurazan and some derivatives that give adducts at the 5-position. The intrinsic rate constant, ko, for this process has a value of 1.5 ± 0.5. The 5-adducts undergo methoxide-catalysed elimination of phenylsulfinic acid to yield alkene derivatives and rate

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11

Morrison, James, Peter Wan, John ET Corrie та V. Ranjit Munasinghe. "Chemistry of photogenerated α-hydroxy-p-nitrobenzyl carbanions in aqueous solution: protonation vs. disproportionation". Canadian Journal of Chemistry 81, № 6 (2003): 586–97. http://dx.doi.org/10.1139/v03-045.

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The photochemistry of p-nitrobenzyl derivatives 610 has been studied in aqueous solution as a function of pH, using product analysis, UVvis spectrophotometry, and laser flash photolysis (LFP). The compounds were chosen with the aim of further exploring the propensity of these systems to give rise to α-hydroxy-p-nitrobenzyl carbanions on photolysis, and to study their mechanisms of subsequent reaction. α-Hydroxy-substituted carbanions are anions that cannot be readily formed using thermal routes but which are believed to have some interesting chemistry. Three methods were employed for photoge

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12

Rios, Ana, AnnMarie C. O'Donoghue, Tina L. Amyes, and John P. Richard. "Formation and stability of organic zwitterions The carbon acid pKas of the trimethylsulfonium and tetramethylphosphonium cations in water." Canadian Journal of Chemistry 83, no. 9 (2005): 1536–42. http://dx.doi.org/10.1139/v05-155.

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We report second-order rate constants of kDO = 7.5 × 104 and 9.9 × 105 (mol/L)1 s1 for exchange for deuterium of the first methyl proton of the trimethylsulfonium and tetramethylphosphonium cations, respectively, in D2O at 25 °C and I = 1.0 (KCl). The data were analyzed to give the following carbon acidities for these cationic carbon acids in water: (CH3)3S+, pKa = 28.5; (CH3)4P+, pKa = 29.4. These acidities are close to those of the neutral carbon acids acetonitrile and dimethylacetamide. This provides evidence that a portion of the stabilization of the cyanomethyl carbanion is due to res

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13

Senatore, Raffaele, Laura Ielo, Serena Monticelli, Laura Castoldi та Vittorio Pace. "Weinreb Amides as Privileged Acylating Agents for Accessing α-Substituted Ketones". Synthesis 51, № 14 (2019): 2792–808. http://dx.doi.org/10.1055/s-0037-1611549.

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The acylation of α-substituted carbanion-type reagents (MCR1R2X; X = halogen, OR, SR, NR3R4, SeR, etc.) with Weinreb amides constitutes a highly versatile and flexible approach for accessing α-functionalized ketones. In this short review we will present a series of transformations—from our own and the work of others—documenting the general applicability of the methodology. Chemoselectivity is uniformly manifested including for critical substrates featuring additional electrophilic functionalities or sterically demanding elements. Importantly, the stereochemical information contained in the Wei

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14

Haynes, RK, PA Schober та MR Binns. "The Aprotic Conjugate Addition-Reactions of the Carbanions of Octenyl Sulfides and Thiocarbamates With γ-Crotonolactone- Stereochemical and Mechanistic Aspects of Reactions Conducted in the Absence and Presence of Hexamethylphosphoric Triamide". Australian Journal of Chemistry 40, № 7 (1987): 1223. http://dx.doi.org/10.1071/ch9871223.

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The lithiated carbanions of (E)- and (Z)-1-(phenylthio)oct-2-ene, (E)-1-(methylthio)oct-2-ene, S-[(E)-oct-2-enyl] N,N-dimethyl( thiocarbamate ), S-[(a-oct-2-enyl] N,N-dimethyl- ( thiocarbamate ), and (E)- and (Z)-1-(phenylsulfony1)oct-2-ene undergo conjugate addition to γ-crotonolactone (but-2-en-4-olide) in tetrahydrofuran at -70� to give as predominant products, syn and anti allylic sulfides, thiocarbamates and sulfones arising from reaction through C1 of the octenyl carbanions . Also formed are smaller amounts of syn and anti vinylic sulfides, thiocarbamates and sulfones arising by reaction

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15

Binns, MR, and RK Haynes. "Stereochemical and Mechanistic Aspects of the Aprotic Conjugate Addition Reactions of the Carbanions of Octenyl Sulfides and Octenyl Thiocarbamates With 4-Tert-Butoxycyclopent-2-Enone in the Presence of Hexamethylphosphoric Triamide." Australian Journal of Chemistry 40, no. 5 (1987): 937. http://dx.doi.org/10.1071/ch9870937.

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The carbanions of (E)- and (Z)-1-(pheny1thio)oct-2-ene, (E)-1-(methy1thio)- and 1-(t-butyl- thio )oct-2-ene, N,N-dimethyl S-[(E)-oct-2-enyllthiocarbamate and (E)-oct-2-enyl benzothiazole undergo conjugate addition to 4-t-butoxycyclopent-2-enone in the presence of hexamethyl - phosphoric triamide ( hmpa ) in tetrahydrofuran at -70� to give as predominant products diastereomeric mixtures of syn and anti allylic sulfides arising from reaction through C1 of the octenyl carbanions. Also formed in some cases are small amounts of diastereomeric mixtures of syn and anti vinylic sulfides arising from r

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16

Farnham, William B. "Fluorinated Carbanions." Chemical Reviews 96, no. 5 (1996): 1633–40. http://dx.doi.org/10.1021/cr9411435.

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17

Ostrowski, Stanisław, and Krzysztof Wojciechowski. "Reactions of organic anions. 174. Vicarious Nucleophilic Substitution of hydrogen (VNS) in nitrobenzofuroxans and the Boulton–Katritzky rearrangement of the VNS products." Canadian Journal of Chemistry 68, no. 12 (1990): 2239–41. http://dx.doi.org/10.1139/v90-344.

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The Vicarious Nucleophilic Substitution of hydrogen in 4-nitrobenzofuroxan derivatives by carbanions of chloromethyl phenyl sulfone, chloromethyl p-tolyl sulfone, chloromethyl tert-butyl sulfone, and N,N-dimethyl chloromethane sulfonamide proceeds at positions 5 and 7. In some cases the Boulton–Katritzky rearrangement of the products obtained, leading to more stable 7-substituted isomers, was observed. Keywords: carbanions, nitrobenzofuroxans, sulfones, Vicarious Nucleophilic Substitution, Boulton–Katritzky rearrangement.

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18

Hayes, Roger N., and John H. Bowie. "Carbanion rearrangements. Collision-induced dissociations of tertiary carbanions derived from alkyl esters." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (1986): 1827. http://dx.doi.org/10.1039/p29860001827.

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19

Bolm, Carsten, Rebekka Bohmann, and Jan-Hendrik Schöbel. "Lithium Sulfondiimidoyl Carbanions." Synlett 27, no. 15 (2016): 2201–4. http://dx.doi.org/10.1055/s-0035-1562725.

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20

Strohmann, Carsten, Bors C. Abele, Klaus Lehmen, et al. "Enantiomerically enriched ‘carbanions’:." Journal of Organometallic Chemistry 661, no. 1-2 (2002): 149–58. http://dx.doi.org/10.1016/s0022-328x(02)01825-9.

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21

Ceccon, Alberto, Alessandro Gambaro, and Alfonso Venzo. "Metal stabilized carbanions." Journal of Organometallic Chemistry 281, no. 2-3 (1985): 221–28. http://dx.doi.org/10.1016/0022-328x(85)87111-4.

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22

Ceccon, Alberto, Alessandro Gambaro, Alfonso Venzo, Vittorio Lucchini, Thomas E. Bitterwolf, and Joyce Shade. "Metal stabilized carbanions." Journal of Organometallic Chemistry 349, no. 3 (1988): 315–22. http://dx.doi.org/10.1016/0022-328x(88)87026-8.

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23

Ceccon, Alberto, Alessandro Gambaro, Francesca Gottardi, Saverio Santi, and Alfonso Venzo. "Metal stabilized carbanions." Journal of Organometallic Chemistry 412, no. 1-2 (1991): 85–94. http://dx.doi.org/10.1016/0022-328x(91)86045-r.

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24

He, Bing, Bingke Li, and Hongwei Zhou. "Theoretical Study on Pyramidal C7N6–H3R3 Molecules." Australian Journal of Chemistry 72, no. 7 (2019): 501. http://dx.doi.org/10.1071/ch19015.

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The pyramidal molecule C7N6H6 and its nine symmetric tri-substituted derivatives C7N6–H3R3 (R=OH, F, CN, N3, NH2, NO2, N=NH, N2H3, and C≡CH) were investigated computationally using the GAUSSIAN 09 program package. Natural bond orbital and atoms in molecules analyses, as well as valence bond theory were applied to investigate the bonding properties. In comparison to their well known analogues C6N7–R3, i.e. generic heptazines, it is found that these 10 molecules are all reactive. Further studies on the topological structures and ionization energy values indicate that the reactive site of the mol

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25

King, James F., Manqing Li, Allan Zijun Cheng, Vinod Dave та Nicholas C. Payne. "Variation of the ease of α-sulfonyl carbanion formation with the orientation of different β-substituents: Experimental evidence for the generality of negative hyperconjugation as an important substituent effect". Canadian Journal of Chemistry 81, № 6 (2003): 638–46. http://dx.doi.org/10.1139/v03-015.

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Following up on our previous observation that the rate of formation of a β-alkoxy-substituted α-sulfonyl carbanion depends on the stereochemistry of the alkoxy group, we have found similar behaviour when the β-substituent is R2N, RS, or R3N+. With each substituent, the variation of kN (defined by kN = (kexch)X /(kexch)model) is consistent with an equation of the form log kN = a + b cos2θ, where θ is the H-C-C-X torsion angle. We propose that the a term describes the polar (field plus inductive) effect and the b term the negative hyperconjugative effect of the substituent; we show how the varia

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26

Jayaweera, H. D. A. Chathumal, Md Mamdudur Rahman, Perry J. Pellechia, Mark D. Smith, and Dmitry V. Peryshkov. "Free three-dimensional carborane carbanions." Chemical Science 12, no. 31 (2021): 10441–47. http://dx.doi.org/10.1039/d1sc02252k.

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27

Donabauer, Karsten, Mitasree Maity, Anna Lucia Berger, Gregory S. Huff, Stefano Crespi, and Burkhard König. "Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols." Chemical Science 10, no. 19 (2019): 5162–66. http://dx.doi.org/10.1039/c9sc01356c.

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28

Ginsburg, Jack Leon, Katherine Valenta Darvesh, Patricia Axworthy, and Richard Francis Langler. "An Ab Initio Molecular Orbital Study of Sulfur-Substituted Carbanions: Toward an Understanding of Regiochemistry in the Chlorination of Unsymmetrical Sulfides." Australian Journal of Chemistry 50, no. 6 (1997): 517. http://dx.doi.org/10.1071/c96187.

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Moller-Plesset molecular orbital calculations at the 6-31+G(d) level have been completed on substituted dimethyl sulfide-derived carbanions. The results are applied to the prediction of regiochemistry for chlorination of unsymmetrical sulfides. Notwithstanding the need for future improvements, regiochemical predictions based on stabilities of sulfur-substituted carbanions match experimental results better than earlier predictions based on stabilities of sulfur-substituted carbonium ions or sulfur-substituted free radicals. The present results suggest that the mechanism for the elimination step

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29

Shindo, Mitsuru. "Ynolates as Functional Carbanions." Synthesis, no. 15 (2003): 2275–88. http://dx.doi.org/10.1055/s-2003-42417.

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30

Barry III, Clif E., Robert B. Bates, William A. Beavers, et al. "Delocalized Carbanions in Synthesis." Synlett 1991, no. 04 (1991): 207–12. http://dx.doi.org/10.1055/s-1991-20682.

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31

Erdik, Ender, and Mehmet Ay. "Electrophilic amination of carbanions." Chemical Reviews 89, no. 8 (1989): 1947–80. http://dx.doi.org/10.1021/cr00098a014.

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32

Petrosyan, V. A., M. E. Niyazymbetov, and B. V. Lyalin. "Electrochemical chlorination of carbanions." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 2 (1987): 269–74. http://dx.doi.org/10.1007/bf00959361.

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33

Harder, Sjoerd. "Schlenk's Early “Free” Carbanions." Chemistry - A European Journal 8, no. 14 (2002): 3229. http://dx.doi.org/10.1002/1521-3765(20020715)8:14<3229::aid-chem3229>3.0.co;2-3.

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34

FARNHAM, W. B. "ChemInform Abstract: Fluorinated Carbanions." ChemInform 27, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199646302.

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35

R., T. PARDASANI. "Studies on the Synthesis and Properties of Boron Stabilised Carbanions." Journal of Indian Chemical Society Vol. 74, June 1997 (1997): 433–39. https://doi.org/10.5281/zenodo.5880331.

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Department of Chemistry, University of Rajasthan, Jaipur-302 004  In recent years, one of the most significant developments which has profoundly added new dimensions to the organoboron chemistry has been the production of carbanions <em>α</em>-to boron. One attractive approach for production of carbanions involves the use of highly hindered organoboranes such as dimesitylmethylborane. On this basis a large number of bifunctional boron complexes of the type Mes<sub>2</sub>BCH<sub>2</sub>MetR<sub>x</sub> have been synthesised. Salient features of their synthesis and applications

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36

Liu, Feng, Jiaxin Tian, Yong Liu та ін. "Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde". Organic Chemistry Frontiers 4, № 8 (2017): 1586–89. http://dx.doi.org/10.1039/c6qo00846a.

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37

Katritzky, Alan R., Christophe Chassaing, Dorin Toader, and Katherine Gill. "Reactions of 1-(Benzotriazol-1-yl)-1-phenoxyalkane and (Benzotriazol-1-yl)ethoxy-phenylmethane Anions with Nitroarenes: A New Approach to Alkyl and Aryl p-Nitroaryl Ketones." Journal of Chemical Research 23, no. 8 (1999): 504–5. http://dx.doi.org/10.1177/174751989902300825.

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38

Berger, Anna Lucia, Karsten Donabauer, and Burkhard König. "Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions." Chemical Science 10, no. 48 (2019): 10991–96. http://dx.doi.org/10.1039/c9sc04987h.

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39

Trost, Barry M., Zhiwei Jiao, and Hadi Gholami. "Palladium-catalyzed asymmetric allylic alkylation (AAA) with alkyl sulfones as nucleophiles." Chemical Science 12, no. 31 (2021): 10532–37. http://dx.doi.org/10.1039/d1sc02599f.

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A variety of “hard” α-sulfonyl carbanions of aryl, heteroaryl and alkyl sulfones were successfully employed as nucleophiles in palladium-catalyzed asymmetric allylic alkylation with excellent enantioselectivities.

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40

Ostrowski, Stanisław, Sylwia Ostrysz, and Agnieszka Mikus. "Porphyrin Complexes with Highly Electronegative Metals - A New Chapter in Nucleophilic Substitution of Hydrogen?" International Journal of Sciences Volume 3, no. 2014-02 (2014): 99–106. https://doi.org/10.5281/zenodo.3348643.

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The attempts of direct substitution of hydrogen in porphyrin macrocyclic systems, with carbanions of weak nucleophilicity, are described. Porphyrins, when converted into the corresponding metal chelates, were reacted with the above mentioned carbanions, and the coordinated central metal atom (e.g., AuIII, SnIV), which reveals considerable electronegativity, played a role of activating group. It could be easily removed from the system after reaction. A number of attempts to substitute hydrogen by carbon nucleophiles led to various products (addition of nucleophile to porphyrin ring, ligands sub

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41

Liu, Shen, Wenteng Chen, Jing Luo, and Yongping Yu. "[3+3] annulation of allylic phosphoryl-stabilized carbanions/phosphorus ylides and vinyl azides: a practice strategy for synthesis of polyfunctionalized anilines." Chem. Commun. 50, no. 62 (2014): 8539–42. http://dx.doi.org/10.1039/c4cc03462g.

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Tandem Michael addition and Witting or Horner–Wadsworth–Emmons olefination initiated [3+3] annulation between vinyl azides and allylic phosphorus ylides or allylic phosphoryl-stabilized carbanions has been developed.

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42

Moss, Robert A., Min Zhang, and Karsten Krogh-Jespersen. "The Trichloromethide and Bromodichloromethide Carbanions." Organic Letters 11, no. 24 (2009): 5702–4. http://dx.doi.org/10.1021/ol902479x.

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43

Motoyoshiya, Jiro, Yutaka Takaguchi, and Hiromu Aoyama. "Chemiluminescent Autoxidation of Phosphonate Carbanions." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 8-9 (2002): 1977–79. http://dx.doi.org/10.1080/10426500213411.

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44

Sasamoto, Ozora. "Catalytic Generation of Superbasic Carbanions." Journal of Synthetic Organic Chemistry, Japan 82, no. 8 (2024): 825–26. http://dx.doi.org/10.5059/yukigoseikyokaishi.82.825.

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45

Tian, Zhixin, and Steven R. Kass. "Carbanions in the Gas Phase." Chemical Reviews 113, no. 9 (2013): 6986–7010. http://dx.doi.org/10.1021/cr4000896.

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46

Berlin, A., S. Bradamante, R. Ferraccioli, and G. A. Pagani. "Trigonal configuration of disulphonyl carbanions." Journal of the Chemical Society, Chemical Communications, no. 15 (1986): 1191. http://dx.doi.org/10.1039/c39860001191.

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47

Ponthieux, Sylvain, and Claude Paulmier. "ChemInform Abstract: Selenium-Stabilized Carbanions." ChemInform 31, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.200029248.

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48

Zwaard, A. W., and H. Kloosterziel. "Some stable substituted cycloheptatrienyl carbanions." Recueil des Travaux Chimiques des Pays-Bas 100, no. 3 (2010): 126–28. http://dx.doi.org/10.1002/recl.19811000312.

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49

Ofial, Armin R., and Herbert Mayr. "Reactivities of Carbocations and Carbanions." Macromolecular Symposia 215, no. 1 (2004): 353–68. http://dx.doi.org/10.1002/masy.200451127.

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50

Comasseto, Joao V., Alcindo A. Dos Santos, and Edison P. Wendler. "ChemInform Abstract: Selenium-Stabilized Carbanions." ChemInform 43, no. 27 (2012): no. http://dx.doi.org/10.1002/chin.201227229.

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