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Journal articles on the topic 'Nucleophilic addition'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 June 2025

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1

Tsuji, Yutaka, and John P. Richard. "Swain–Scott relationships for nucleophile addition to ring-substituted phenonium ions." Canadian Journal of Chemistry 93, no. 4 (2015): 428–34. http://dx.doi.org/10.1139/cjc-2014-0337.

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The products of the reactions of 2-(4-methoxyphenyl)ethyl tosylate (MeO-1-OTs) and 2-(4-methyphenyl)ethyl tosylate (Me-1-OTs) with nucleophilic anions were determined for reactions in 50:50 (v/v) trifluoroethanol (TFE) / water at 25 °C. In many cases, the nucleophile selectivity kNu/ks ((mol/L)−1) for reactions of nucleophile and solvent, calculated from the ratio of product yields, depends upon [Nu−]. This demonstrates the existence of competing reaction pathways, which show different selectivities for reactions with nucleophiles. A 13C NMR analysis of the products of the reactions of substrate enriched with 13C at the α-carbon, X-1-[α-13C]OTs (X = −OCH3 or −Me), with nucleophilic anions in 50:50 (v/v) TFE/water at 25 °C shows the formation of X-1-[β-13C]OH, X-1-[β-13C]OCH2CF3, and X-1-[β-13C]Nu (Nu = Br, Cl, CH3CO2, or Cl2CHCO2) from the trapping of symmetrical phenonium ion reaction intermediates X-2+. The observation of excess label in the α-position, [α-13C]/[β-13C] > 1.0, for both the water and nucleophile adducts, shows that these nucleophiles also react by direct substitution at X-1-[α-13C]OTs. The ratios of product yields, [α-13C]/[β-13C], and observed nucleophile selectivity (kNu/ks)obs were used to dissect the contribution of nucleophile addition at Me-1-OTs and trapping of X-2+ to the product yields. The product yields from partitioning of the intermediate gave the nucleophile selectivity kNu/ks for X-2+. Swain–Scott plots of log(kNu/ks) are correlated by slopes of s = 0.78 and s = 0.73 for reactions of MeO-2+ and Me-2+, respectively. This shows that the sensitivity of bimolecular substitution at X-2+ to changes in nucleophile reactivity is smaller than for nucleophilic substitution at the methyl iodide.

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2

Sengee, Myagmarsuren, та Leiv K. Sydnes. "Specific conjugate addition to α,β-acetylenic ketones". Pure and Applied Chemistry 83, № 3 (2011): 587–96. http://dx.doi.org/10.1351/pac-con-10-10-24.

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A variety of α,β-unsaturated acetylenic ketones, prepared in good yields from 3,3,4,4-tetraethoxybut-1-yne (TEB), have been reacted with selected mono- and bis-nucleophilic reagents. The mononucleophiles react in a Michael fashion and give in most cases the corresponding α,β-unsaturated alkenones in good yield. Many of the alkenes are formed as single stereoisomers, but the configuration depends on the nature of the nucleophile. If hydrogen bonds can be formed, the Z geometry is preferred, otherwise the E geometry is completely predominant. Experiments have also uncovered that α,β-unsaturated acetylenic ketones with a gem-diethoxy moiety in the α' position decompose when reacted with sodium hydroxide in aqueous tetrahydrofuran (THF); the carbonyl group is attacked and a carboxylic acid and a terminal alkyne are formed. If the nucleophiles contain two nucleophilic centers or if the α,β-unsaturated acetylenic ketones contain an additional reactive group, such as a hydroxyl group or an acyloxy moiety, useful secondary reactions may occur. By taking advantage of such secondary transformations, two completely regioselective syntheses of furans have so far been developed.

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3

Zhang, Yanbin, Ruiwen Jin, Guangxing Pan, and Hao Guo. "Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes." Chemical Communications 56, no. 78 (2020): 11621–24. http://dx.doi.org/10.1039/d0cc04636a.

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4

Song, Wangze, Ming Li, Junnan He, Junhao Li, Kun Dong, and Yubin Zheng. "Copper-catalyzed tandem annulation/enol nucleophilic addition to access multisubstituted indoles." Organic & Biomolecular Chemistry 17, no. 10 (2019): 2663–69. http://dx.doi.org/10.1039/c9ob00181f.

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5

Imada, Yasushi, Yukihiro Arakawa, Shun Ueta, Takuma Okamoto, and Keiji Minagawa. "Nucleophilic Addition to Nitrones Using a Flow Microreactor." Synlett 31, no. 09 (2020): 866–70. http://dx.doi.org/10.1055/s-0039-1691601.

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Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch conditions resulted in lower yields because of undesired side reactions.

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6

Kutschy, Peter, Pavol Kristian, Milan Dzurilla, Dušan Koščík, and Róbert Nádaskay. "Selectivity of nucleophilic addition to and substitution at isothiocyanatocarbonyl group. Reactions of 4-pentinoyl- and 2-(2-propinyl)-4-pentinoyl isothiocyanate with amines and methanol." Collection of Czechoslovak Chemical Communications 52, no. 4 (1987): 995–1005. http://dx.doi.org/10.1135/cccc19870995.

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4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides. The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureas only. Both isothiocyanates afford with methanol as a nucleophile exclusively the corresponding O-methyl monothiocarbamates.

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7

Rani, Poonam, and Rajendra Srivastava. "Nucleophilic addition of amines, alcohols, and thiophenol with epoxide/olefin using highly efficient zirconium metal organic framework heterogeneous catalyst." RSC Advances 5, no. 36 (2015): 28270–80. http://dx.doi.org/10.1039/c5ra00921a.

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8

Nishi, Takafumi, Isao Mizota, and Makoto Shimizu. "Integrated reactions using addition to conjugated imines and iminium salts." Pure and Applied Chemistry 84, no. 12 (2012): 2609–17. http://dx.doi.org/10.1351/pac-con-12-01-03.

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Recently, nucleophilic addition reactions to imino functions have been utilized in many crucial steps for the synthesis of bioactive and functional materials. This article summarizes the integrated “umpolung” reactions of α-imino esters and the use of iminium salts as reactive electrophiles. Regarding the umpolung reactions, the following five reactions are discussed: (1) N-alkylation/homocoupling; (2) tandem N-ethylation/C-allylation; (3) tandem N-ethylation/C-cyanation; (4) reduction of imines with tris(trimethylsilyl)aluminum; and (5) N-alkylation and Claisen rearrangement. Moreover, the generation and reactions of alkoxycarbonyl iminium species are also discussed. These are prepared easily from trisubstituted amino ketene silyl acetals by oxidation, and the subsequent nucleophilic addition of various nucleophiles readily affords the addition products.

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9

Edwards, Andrew, Marina Rubina, and Michael Rubin. "Nucleophilic Addition of Cyclopropenes." Current Organic Chemistry 20, no. 18 (2016): 1862–77. http://dx.doi.org/10.2174/1385272820666160331235409.

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10

Gao, Yu-Qi, Yi Hou, Liming Zhu, et al. "Visible-light driven synthesis of polycyclic benzo[d][1,3]oxazocine from 2-aminochalcone." Chemical Communications 56, no. 49 (2020): 6739–42. http://dx.doi.org/10.1039/d0cc02416c.

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11

Charushin, V. N., and O. N. Chupakhin. "SNH methodology and new approaches to condensed heterocyclic systems." Pure and Applied Chemistry 76, no. 9 (2004): 1621–31. http://dx.doi.org/10.1351/pac200476091621.

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The review surveys the reactions of electron-deficient azaaromatic compounds with mono- and bifunctional nucleophilies in which a nucleophilic attack at the unsubstituted CH carbon of an aromatic ring is one of the key steps. Use of the SNH methodology for the synthesis of fused heterocyclic systems by means of nucleophilic addition –addition AN–AN, addition –substitution of hydrogen AN–SNH, tandem substitution of hydrogen SNH–SNH, and other strategies will be discussed. Intramolecular SNH reactions will also be considered as effective synthetic tools to obtain condensed heterocyclic systems.

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12

Plé, Nelly, Alain Turck, and Guy Queguiner. "Additions covalentes de nucléophiles sur les pyrido-as-triazines." Canadian Journal of Chemistry 70, no. 11 (1992): 2828–33. http://dx.doi.org/10.1139/v92-359.

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Covalent addition of various nucleophiles to pyrido-as-triazines was studied and the σ-adduct structures were determined by NMR. A remarkable reactivity toward carbon nucleophiles has been highlighted for pyrido-as-triazines bearing a pyridinic nitrogen in the β position: only in the pteridine series has a similar reactivity been encountered. Complete regioselectivity of the nucleophilic attack on the pyridine nucleus peri to the triazine was observed.

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13

Cheng, Huayu, Xiaofan Zhou, Anjing Hu, et al. "Thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes: divergent synthesis from reaction of 2-trifluoromethyl-1,3-conjugated enynes with sulfur nucleophiles." RSC Advances 8, no. 59 (2018): 34088–93. http://dx.doi.org/10.1039/c8ra07834c.

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A divergent synthesis of thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes viaregioselective nucleophilic addition of sulfur nucleophiles to 2-trifluoromethyl-1,3-conjugated enynes was developed.

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14

Zhang, Zhenhui, Lin Li, Yuting Li та ін. "Insight on a Competitive Nucleophilic Addition Reaction of Nε-(Carboxymethyl) Lysine or Different Amino Acids with 4-Methylbenzoquinone". Foods 11, № 10 (2022): 1421. http://dx.doi.org/10.3390/foods11101421.

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ο-benzoquinone is a common intermediate which is mostly formed by the oxidation of phenolics or polyphenols containing catechol structure. ο-benzoquinone has an outstanding nucleophilic ability, while advanced glycation end products (AGEs) are nucleophilic and can undergo a nucleophilic addition reaction with ο-benzoquinone to mitigate the harmful effects of AGEs on the body. As common nucleophilic substances, amino acids existing in large quantities in food processing and in vivo may bind competitively with ο-benzoquinone, thus influencing the trapping of ο-benzoquinone with AGEs. In this study, cyclic voltammetry and coexistence experiments were used to compare the reactivities of Nε-(carboxymethyl) lysine (CML) and amino acids with 4-methylbenzoquinone (4-MBQ). The results showed that CML is more reactive with ο-benzoquinone than most amino acids, and even in complex systems, ο-benzoquinone still captured CML. Moreover, almost all adducts were identified by UPLC-QTOF-MS/MS, and their chemical formulas were deduced. Quantum chemistry accurately predicts the efficiency and site of reactions of ο-benzoquinone and nucleophiles to a certain extent, and found that a secondary amine has a greater reactivity with 4-MBQ than a primary amine in a similar molecular structure. In general, ο-benzoquinone could capture AGEs, thereby showing potential to reduce the harmfulness of AGEs.

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15

Burianova, Valeria K., Dmitrii S. Bolotin, Alexander S. Mikherdov та ін. "Mechanism of generation of closo-decaborato amidrazones. Intramolecular non-covalent B–H⋯π(Ph) interaction determines stabilization of the configuration around the amidrazone CN bond". New Journal of Chemistry 42, № 11 (2018): 8693–703. http://dx.doi.org/10.1039/c8nj01018h.

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16

Sato, Takaaki, and Noritaka Chida. "Nucleophilic addition to N-alkoxyamides." Organic & Biomolecular Chemistry 12, no. 20 (2014): 3147. http://dx.doi.org/10.1039/c4ob00389f.

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17

Yanagita, Yuta, Hugh Nakamura, Kenji Shirokane, Yusuke Kurosaki, Takaaki Sato, and Noritaka Chida. "Direct Nucleophilic Addition toN-Alkoxyamides." Chemistry - A European Journal 19, no. 2 (2012): 678–84. http://dx.doi.org/10.1002/chem.201202639.

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18

Santos, A. Mafalda, M. Fernanda N. N. Carvalho, Adelino M. Galvão, and Armando J. L. Pombeiro. "Reactivity Trends in the Reaction of Alkynes with 3-Oxo-camphorsulfonylimine." Zeitschrift für Naturforschung B 57, no. 6 (2002): 691–98. http://dx.doi.org/10.1515/znb-2002-0616.

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Abstract The regioselective addition of deprotonated alkynes (phenyl-1-propyne, propargyl ether or tetrahydropyran-protected 3-butyn-1-ol) to the imine group was identified as a competitive process to the nucleophilic addition to the keto group of (1S)-3-oxo-camphorsulfonylimine. The selectivity of the process depends on the characteristics of the nucleophile and the reaction conditions. In the case of propargyl ether it was possible to render the imine addition the main process.The structural characterization of compounds 1, 2, 6 by X-ray diffraction analysis show that the C2 - C3 bond becomes longer upon nucleophilic addition to the imine group of (1S)-3-oxo-camphorsulfonylimine. This trend is believed to favour the ring opening process that undergoes the formation of the spiro type compound 7.

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19

Carramiñana, Victor, Ana M. Ochoa de Retana, Francisco Palacios та Jesús M. de los Santos. "Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells". Molecules 25, № 15 (2020): 3332. http://dx.doi.org/10.3390/molecules25153332.

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This work reports a straightforward regioselective synthetic methodology to prepare α-aminophosphine oxides and phosphonates through the addition of oxygen and sulfur nucleophiles to the C–N double bond of 2H-azirine derivatives. Determined by the nature of the nucleophile, different α-aminophosphorus compounds may be obtained. For instance, aliphatic alcohols such as methanol or ethanol afford α-aminophosphine oxide and phosphonate acetals after N–C3 ring opening of the intermediate aziridine. However, addition of 2,2,2-trifluoroethanol, phenols, substituted benzenthiols or ethanethiol to 2H-azirine phosphine oxides or phosphonates yields allylic α-aminophosphine oxides and phosphonates in good to high general yields. In some cases, the intermediate aziridine attained by the nucleophilic addition of O- or S-nucleophiles to the starting 2H-azirine may be isolated and characterized before ring opening. Additionally, the cytotoxic effect on cell lines derived from human lung adenocarcinoma (A549) and non-malignant cells (MCR-5) was also screened. Some α-aminophosphorus derivatives exhibited very good activity against the A549 cell line in vitro. Furthermore, selectivity towards cancer cell (A549) over non-malignant cells (MCR-5) has been detected in almost all compounds tested.

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20

Birdsall, A. W., C. R. Miner, L. E. Mael, and M. J. Elrod. "Mechanistic study of secondary organic aerosol components formed from nucleophilic addition reactions of methacrylic acid epoxide." Atmospheric Chemistry and Physics Discussions 14, no. 14 (2014): 19917–54. http://dx.doi.org/10.5194/acpd-14-19917-2014.

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Abstract. Recently, methacrylic acid epoxide (MAE) has been proposed as a precursor to an important class of isoprene-derived compounds found in secondary organic aerosol (SOA): 2-methylglyceric acid (2-MG) and a set of oligomers, nitric acid esters and sulfuric acid esters related to 2-MG. However, the specific chemical mechanisms by which MAE could form these compounds have not been previously studied. In order to determine the relevance of these processes to atmospheric aerosol, MAE and 2-MG have been synthesized and a series of bulk solution-phase experiments aimed at studying the reactivity of MAE using nuclear magnetic resonance (NMR) spectroscopy have been performed. The present results indicate that the acid-catalyzed MAE reaction is more than 600 times slower than a similar reaction of an important isoprene-derived epoxide, but is still expected to be kinetically feasible in the atmosphere on more acidic SOA. The specific mechanism by which MAE leads to oligomers was identified, and the reactions of MAE with a number of atmospherically relevant nucleophiles were also investigated. Because the nucleophilic strengths of water, sulfate, alcohols (including 2-MG), and acids (including MAE and 2-MG) in their reactions with MAE were found to be of a similar magnitude, it is expected that a diverse variety of MAE + nucleophile product species may be formed on ambient SOA. Thus, the results indicate that epoxide chain reaction oligomerization will be limited by the presence of high concentrations of non-epoxide nucleophiles (such as water); this finding is consistent with previous environmental chamber investigations of the relative humidity-dependence of 2-MG-derived oligomerization processes and suggests that extensive oligomerization may not be likely on ambient SOA because of other competitive MAE reaction mechanisms.

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21

Birdsall, A. W., C. R. Miner, L. E. Mael, and M. J. Elrod. "Mechanistic study of secondary organic aerosol components formed from nucleophilic addition reactions of methacrylic acid epoxide." Atmospheric Chemistry and Physics 14, no. 23 (2014): 12951–64. http://dx.doi.org/10.5194/acp-14-12951-2014.

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Abstract. Recently, methacrylic acid epoxide (MAE) has been proposed as a precursor to an important class of isoprene-derived compounds found in secondary organic aerosol (SOA): 2-methylglyceric acid (2-MG) and a set of oligomers, nitric acid esters, and sulfuric acid esters related to 2-MG. However, the specific chemical mechanisms by which MAE could form these compounds have not been previously studied with experimental methods. In order to determine the relevance of these processes to atmospheric aerosol, MAE and 2-MG have been synthesized and a series of bulk solution-phase experiments aimed at studying the reactivity of MAE using nuclear magnetic resonance (NMR) spectroscopy have been performed. The present results indicate that the acid-catalyzed MAE reaction is more than 600 times slower than a similar reaction of an important isoprene-derived epoxide, but is still expected to be kinetically feasible in the atmosphere on more acidic SOA. The specific mechanism by which MAE leads to oligomers was identified, and the reactions of MAE with a number of atmospherically relevant nucleophiles were also investigated. Because the nucleophilic strengths of water, sulfate, alcohols (including 2-MG), and acids (including MAE and 2-MG) in their reactions with MAE were found to be of similar magnitudes, it is expected that a diverse variety of MAE + nucleophile product species may be formed on ambient SOA. Thus, the results indicate that epoxide chain reaction oligomerization will be limited by the presence of high concentrations of non-epoxide nucleophiles (such as water); this finding is consistent with previous environmental chamber investigations of the relative humidity dependence of 2-MG-derived oligomerization processes and suggests that extensive oligomerization may not be likely on ambient SOA because of other competitive MAE reaction mechanisms.

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22

Rosenberg, Michal, Štefan Baláž, Ernest Šturdík, and Anton Kuchár. "Reactivity of 2-furylethylenes with nucleophilic groups and its biological significance." Collection of Czechoslovak Chemical Communications 52, no. 2 (1987): 425–30. http://dx.doi.org/10.1135/cccc19870425.

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The paper describes addition-nucleophilic reactions of 1-(5-R1-2-furyl)-2-R2-R3-ethylenes with SH (thioglycolic acid), NH2 (glycine) and OH (phenol) nucleophiles, and with hydroxyl ions in aqueous media. The determined rate constants, of second order (dm3 mol-1 s-1), show that in the physiological conditions the preferential reaction will be that with thiols. The amino acid composition of proteins modified with 1-(5-nitro-2-furyl)-2-nitro-2-methoxycarbonylethylene has revealed that the only group affected was the SH group of cysteine. This finding points out the significance of addition-nucleophilic SH-interactions of 2-furylethylenes with the protein macromolecules and accounts for the high cytotoxicity of these compounds.

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23

Marchois, J., C. Fressigné, B. Lecachey, and J. Maddaluno. "Base or nucleophile? DFT finally elucidates the origin of the selectivity between the competitive reactions triggered by MeLi or LDA on propanal." Chemical Communications 51, no. 48 (2015): 9801–4. http://dx.doi.org/10.1039/c5cc01549a.

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Why is LDA such a good base while MeLi is mainly a nucleophile? This communication presents a DFT theoretical study comparing side by side the mechanistic pathways followed during the deprotonation and nucleophilic addition of these two reagents, solvated by THF, onto propanal.

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24

Yamagishi, Masahito, Jun Okazaki, Ken Nishigai, Takeshi Hata, and Hirokazu Urabe. "Additive-Free Nucleophilic Addition of Imidazolines and Imidazoles to Haloacetylenes." Organic Letters 14, no. 1 (2011): 34–37. http://dx.doi.org/10.1021/ol2027448.

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25

Topanov, P. A., I. V. Mashevskaya, M. V. Dmitriev, and A. N. Maslivets. "Nucleophilic Addition of Oxindole to Pyrrolobenzoxazinetriones." Russian Journal of Organic Chemistry 57, no. 1 (2021): 126–30. http://dx.doi.org/10.1134/s107042802101019x.

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26

Carlsen, Per H. J., Kristin Aase, Carl Axel Wachtmeister, et al. "Nucleophilic Addition to Cyclic 1,2-Sulfites." Acta Chemica Scandinavica 47 (1993): 617–19. http://dx.doi.org/10.3891/acta.chem.scand.47-0617.

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27

Topanov, P. A., I. V. Mashevskaya, M. V. Dmitriev, and A. N. Maslivets. "Nucleophilic Addition of Oxindole to Pyrroloquinoxalinetriones." Russian Journal of Organic Chemistry 56, no. 4 (2020): 719–22. http://dx.doi.org/10.1134/s1070428020040247.

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28

Tian, Panpan, Cheng-Qiang Wang, Sai-Hu Cai, et al. "F– Nucleophilic-Addition-Induced Allylic Alkylation." Journal of the American Chemical Society 138, no. 49 (2016): 15869–72. http://dx.doi.org/10.1021/jacs.6b11205.

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29

Rose-Munch, F., and K. Aniss. "Cationic arenetricarbonylmanganese complexes : nucleophilic aromatic addition." Tetrahedron Letters 31, no. 44 (1990): 6351–54. http://dx.doi.org/10.1016/s0040-4039(00)97061-8.

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30

Birri, Anthony, Jonathan W. Steed, and Derek A. Tocher. "Nucleophilic addition to ruthenium activated tetramethylthiophene." Journal of Organometallic Chemistry 575, no. 2 (1999): 242–45. http://dx.doi.org/10.1016/s0022-328x(98)01000-6.

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31

Chambers, Richard D., Andrew R. Edwards, Andrei Batsanov, and Judith A. K. Howard. "Ambident nucleophilic addition to ethyl trifluoromethylacetoacetate." Journal of Fluorine Chemistry 88, no. 1 (1998): 95–97. http://dx.doi.org/10.1016/s0022-1139(98)00124-9.

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32

Rose-Munch, Françoise, Laurent Mignon, and Jean Paul Souchez. "Double nucleophilic addition to fluoroarenetricarbonylchromium complexes." Tetrahedron Letters 32, no. 44 (1991): 6323–24. http://dx.doi.org/10.1016/0040-4039(91)80158-3.

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33

Stanic, Ana, Silvio Uhlig, Anita Solhaug, Frode Rise, Alistair L. Wilkins, and Christopher O. Miles. "Nucleophilic Addition of Thiols to Deoxynivalenol." Journal of Agricultural and Food Chemistry 63, no. 34 (2015): 7556–66. http://dx.doi.org/10.1021/acs.jafc.5b02864.

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34

Zhao, Yu, Zitong Zhou, Man Chen, and Weiguang Yang. "Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides." Molecules 26, no. 12 (2021): 3700. http://dx.doi.org/10.3390/molecules26123700.

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N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.

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35

TIWARI, R. K., A. K. SAXENA, and P. S. VENKATARAMANI. "ChemInform Abstract: Nucleophilic Addition to Aryl Ethynyl Ketone: Addition of Oxygen Containing Nucleophiles to Terephthaloyl Acetylene." ChemInform 28, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199713065.

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36

Vanarsdale, W. E., R. E. K. Winter, and J. K. Kochi. "Nucleophilic addition to coordinated allyl ligands. Heteroatom nucleophiles with cationic molybdenum complexes." Journal of Organometallic Chemistry 296, no. 1-2 (1985): 31–54. http://dx.doi.org/10.1016/0022-328x(85)80337-5.

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37

Fang, Xiang, Yong-Ming Wu, Juan Deng, and Shao-Wu Wang. "The nucleophilic addition reactions of difluorovinyl tosylates with O- and S-nucleophiles." Journal of Fluorine Chemistry 125, no. 10 (2004): 1481–84. http://dx.doi.org/10.1016/j.jfluchem.2004.05.014.

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38

Lakhdar, Sami, Guillaume Berionni, and François Terrier. "Superelectrophilicity in Michael-Type Reactions: Water Addition to 4-Nitrobenzodifuroxan." Synthesis 49, no. 15 (2017): 3453–59. http://dx.doi.org/10.1055/s-0036-1590839.

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Kinetic and thermodynamic measurements of the ease of covalent hydration of 4-nitrobenzodifuroxan (NBDF) to give the corresponding hydroxy adduct has been carried out over a large pH range of 0.82–12.23 in aqueous solution. A most important result is that water is the sole efficient nucleophile contributing to the hydration of this peculiar nitroolefin in the pH range 4–8. Based on this finding as well as a pK a H2O value of 2.85 for the complexation process there is no doubt that the electrophilic character of NBDF falls in the domain of superelectrophilicity defined with reference to covalent nucleophilic additions to 4,6-dinitrobenzofuroxan (DNBF; pK a H2O = 3.75) and related heterocycles. This also corresponds to a positioning of NBDF at the top of the electrophilicity scale E introduced by Mayr to describe the feasibility of nucleophilic-electrophilic combinations. Returning to the hydration of the series of activated olefins, it has been possible to expand the domain of reactivity of Michael acceptors by six orders of magnitude, going from benzylidenemalonitrile (pK a H2O = 10.70; E = –9.42) to the para-nitro-substituted benzylidene Meldrum’ s acid (pK a H2O = 3.46; E = –5.49). The positioning of these olefins on the pK a scale shows that not only 4-nitrobenzodifuroxan but also the unsubstituted Meldrum’s acid are located in the superelectrophilic region.

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39

Damas, Liliana, Rui M. B. Carrilho, Sandra C. C. Nunes, et al. "A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis- N -heterocycles: rationalization by electronic structure calculations." Royal Society Open Science 5, no. 9 (2018): 181140. http://dx.doi.org/10.1098/rsos.181140.

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An unprecedented palladium-catalysed sequential aminocarbonylation/cyclization synthetic strategy, using carbon monoxide and structurally different aliphatic diamines as N -nucleophiles, gives access, in one pot, to a new family of indole-based N -heterocyclic derivatives (hydropyrazinones, benzodiazepinones and hydroquinoxalines). Optimization of the reaction conditions towards double carbonylation ( P CO = 30 bar, T = 80°C, iodoindole/diamine ratio = 1 : 1.5, toluene as solvent) allowed the target cyclic products, which are formed in situ via intramolecular cyclization of the ketocarboxamide intermediates, to be obtained through a nucleophilic addition/elimination reaction with the pendant terminal amine groups. The structure of the diamine nucleophile was revealed to affect the reaction's selectivity, with the best yields for the cyclic products being obtained in the presence of (1 S , 2S )-(+)-cyclohexane-1,2-diamine ( a ) as the nucleophile, using either 5- or 7-iodoindole as the substrate. The reaction's selectivity was rationalized based on electronic structure calculations, which explain the effect of the diamine structure on the predominant formation of the cyclic products.

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40

Benchoam, Dayana, Jonathan A. Semelak, Ernesto Cuevasanta, et al. "Acidity and nucleophilic reactivity of glutathione persulfide." Journal of Biological Chemistry 295, no. 46 (2020): 15466–81. http://dx.doi.org/10.1074/jbc.ra120.014728.

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Persulfides (RSSH/RSS−) participate in sulfur trafficking and metabolic processes, and are proposed to mediate the signaling effects of hydrogen sulfide (H2S). Despite their growing relevance, their chemical properties are poorly understood. Herein, we studied experimentally and computationally the formation, acidity, and nucleophilicity of glutathione persulfide (GSSH/GSS−), the derivative of the abundant cellular thiol glutathione (GSH). We characterized the kinetics and equilibrium of GSSH formation from glutathione disulfide and H2S. A pKa of 5.45 for GSSH was determined, which is 3.49 units below that of GSH. The reactions of GSSH with the physiologically relevant electrophiles peroxynitrite and hydrogen peroxide, and with the probe monobromobimane, were studied and compared with those of thiols. These reactions occurred through SN2 mechanisms. At neutral pH, GSSH reacted faster than GSH because of increased availability of the anion and, depending on the electrophile, increased reactivity. In addition, GSS− presented higher nucleophilicity with respect to a thiolate with similar basicity. This can be interpreted in terms of the so-called α effect, i.e. the increased reactivity of a nucleophile when the atom adjacent to the nucleophilic atom has high electron density. The magnitude of the α effect correlated with the Brønsted nucleophilic factor, βnuc, for the reactions with thiolates and with the ability of the leaving group. Our study constitutes the first determination of the pKa of a biological persulfide and the first examination of the α effect in sulfur nucleophiles, and sheds light on the chemical basis of the biological properties of persulfides.

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41

El-Shishtawy, Reda M., Manal M. El-Zawahry, Fatma Abdelghaffar, and Nahed S. E. Ahmed. "Nucleophilic Addition of Reactive Dyes on Amidoximated Acrylic Fabrics." Scientific World Journal 2014 (2014): 1–11. http://dx.doi.org/10.1155/2014/305930.

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Seven reactive dyes judiciously selected based on chemical structures and fixation mechanisms were applied at 2% owf of shade on amidoximated acrylic fabrics. Amidoximated acrylic fabric has been obtained by a viable amidoximation process. The dyeability of these fabrics was evaluated with respect to the dye exhaustion, fixation, and colour strength under different conditions of temperature and dyeing time. Nucleophilic addition type reactive dyes show higher colour data compared to nucleophilic substitution ones. FTIR studies further implicate the binding of reactive dyes on these fabrics. A tentative mechanism is proposed to rationalize the high fixation yield obtained using nucleophilic addition type reactive dyes. Also, the levelling and fastness properties were evaluated for all dyes used. Excellent to good fastness and levelling properties were obtained for all samples irrespective of the dye used. The result of investigation offers a new method for a viable reactive dyeing of amidoximated acrylic fabrics.

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42

Yamanushkin, Pavel, Michael Lu-Diaz, Andrew Edwards, Nicolai A. Aksenov, Marina Rubina, and Michael Rubin. "Correction: Directed nucleophilic addition of phenoxides to cyclopropenes." Organic & Biomolecular Chemistry 16, no. 31 (2018): 5719. http://dx.doi.org/10.1039/c8ob90109k.

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43

Liu, Yu-Wei, Ye-Hui Chen, Jun Kee Cheng, Shao-Hua Xiang, and Bin Tan. "Enantioselective synthesis of 3-arylindole atropisomers via organocatalytic indolization of iminoquinones." Chemical Synthesis 3, no. 2 (2023): 11. http://dx.doi.org/10.20517/cs.2022.46.

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The direct enantioselective construction of axially chiral 3-arylindole frameworks via nucleophilic addition of 2-substituted indoles to iminoquinones has been achieved with high efficiencies under mild chiral phosphoric acid (CPA) catalytic conditions. The utility of this method was demonstrated in successful scale-up syntheses without compromising the product yields and enantioselectivities. The oxidation of products yields axially chiral heteroaryl-p-quinone monoimine, which could be subjected to structural diversification via addition of nucleophiles.

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44

Laina-Martín, Víctor, Ignacio Pérez, Jose A. Fernández-Salas, and José Alemán. "Nucleophilic halo-Michael addition under Lewis-base activation." Chemical Communications 55, no. 86 (2019): 12936–39. http://dx.doi.org/10.1039/c9cc07068k.

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A simple and general conjugate nucleophilic halogenation is presented. In addition, a straightforward diastereoselective halogen installation using α,β-unsaturated acyloxazolidinones as platforms has been developed.

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45

Bernasconi, Claude F., Rodney J. Ketner, Xin Chen, and Zvi Rappoport. "Detection and kinetic characterization of SNV intermediates. Reactions of thiomethoxybenzylidene Meldrum's acid with thiolate ions, alkoxide ions, OH-, and water in aqueous DMSO." Canadian Journal of Chemistry 77, no. 5-6 (1999): 584–94. http://dx.doi.org/10.1139/v99-009.

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The reaction of thiomethoxybenzylidene Meldrum's acid (5-SMe) with thiolate and alkoxide ion nucleophiles is shown to proceed by the two-step addition-elimination SNV mechanism in which the tetrahedral intermediate accumulates to detectable levels. For the reactions with thiolate ions, rate constants for nucleophilic addition (k1RX), its reverse (k-1RX), and for conversion of the intermediate to products (k2RX) were determined. For the reactions with alkoxide ions, only k1RX and k-1RX could be obtained; the intermediate in these reactions did not yield the expected substitution products, and hence no k2RX values could be determined. The reactions with OH- and water are believed to follow the same mechanism, but the respective intermediates remain at steady-state levels, and only k1OH and k1H²O for nucleophilic attack on 5-SMe were measurable. New insights regarding structure-reactivity behavior in SNV reactions are gained from comparisons of rate and equilibrium constants in the reactions of 5-SMe with the corresponding parameters in the reactions of methoxybenzylidene Meldrum's acid (5-OMe) and benzylidene Meldrum's acid (5-H). In particular, the relative importance of steric and pi-donor effects of the MeS vs. MeO group in 5-SMe and 5-OMe, respectively, and their role in affecting the intrinsic rate constants for nucleophilic addition, has been clarified by these comparisons. Our results also add support to a previous suggestion that soft-soft type interactions tend to increase intrinsic rate constants for thiolate ion addition to vinylic substrates, especially 5-SMe with the soft MeS group.Key words: nucleophilic vinylic substitution, intrinsic rate constants, transition state imbalances, steric/pi-donor/anomeric effects.

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46

Dong, Zhi-Bing, and Jin-Quan Chen. "Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions." Synthesis 52, no. 24 (2020): 3714–34. http://dx.doi.org/10.1055/s-0040-1706550.

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AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organozinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

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47

Melnykov, Serhii, Volodymyr Sukach, and Mykhailo Vovk. "Recent Achievements in Nucleophilic Decarboxylative Addition Reactions." Current Organic Chemistry 24, no. 19 (2020): 2193–215. http://dx.doi.org/10.2174/1385272824999200818181531.

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Decarboxylative addition reactions are well known as an effective approach to C–C bonds formation due to the availability of starting reagents, ease of handling, and low environmental impact. This approach clearly demonstrated its potential for the synthesis of the variety of acyclic and heterocyclic compounds, including optically active ones. The significant amount of articles devoted to this topic published in recent years proves the importance of this approach in modern organic synthesis. In this review, the recent achievements in decarboxylative addition to C=C, C=N, and C=O bonds have been summarized and discussed over the last 6 years.

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48

Afarinkia, Kamyar, Egizia De Pascale, and Sia Amara. "Asymmetric nucleophilic addition to vinylphosphonamidates (Part IV)." Arkivoc 2002, no. 6 (2002): 205–11. http://dx.doi.org/10.3998/ark.5550190.0003.618.

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49

Fu, G., та S. Smith. "Nucleophilic Addition γ to the Carbonyl Group". Synfacts 2009, № 12 (2009): 1407. http://dx.doi.org/10.1055/s-0029-1218215.

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50

Gusarova, N. K., S. I. Verkhoturova, T. I. Kazantseva, et al. "Nucleophilic addition of phosphine to vinyl sulfoxides." Russian Journal of General Chemistry 78, no. 5 (2008): 1011–13. http://dx.doi.org/10.1134/s1070363208050319.

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