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Journal articles on the topic 'Regioselective electrophilic substitution'

Author: Grafiati

Published: 9 March 2023

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1

Smith, Keith, and Gamal El-Hiti. "Regioselective Control of Electrophilic Aromatic Substitution Reactions." Current Organic Synthesis 1, no. 3 (July 1, 2004): 253–74. http://dx.doi.org/10.2174/1570179043366747.

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2

Smith, Keith, and Gamal El-Hiti. "Regioselective Electrophilic Aromatic Substitution Reactions over Reusable Zeolites." Current Organic Chemistry 10, no. 13 (September 1, 2006): 1603–25. http://dx.doi.org/10.2174/138527206778249685.

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3

Smith, Keith. "Highly Regioselective, Lewis Acid-Free Electrophilic Aromatic Substitution." Journal of Chemical Technology & Biotechnology 68, no. 4 (April 1997): 432–36. http://dx.doi.org/10.1002/(sici)1097-4660(199704)68:4<432::aid-jctb617>3.0.co;2-x.

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4

Watanabe, Yutaka, Tsuyoshi Uemura, Satoe Yamauchi, Kousei Tomita, Takafumi Saeki, Ryousuke Ishida, and Minoru Hayashi. "Regioselective functionalization of unprotected myo-inositol by electrophilic substitution." Tetrahedron 69, no. 23 (June 2013): 4657–64. http://dx.doi.org/10.1016/j.tet.2013.03.109.

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5

Somogyi, László. "Synthesis of mixed osazone derivatives by regioselective electrophilic substitution." Carbohydrate Research 152 (September 1986): 316–22. http://dx.doi.org/10.1016/s0008-6215(00)90314-8.

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6

Azzena, Ugo, Giovanni Melloni, Anna Maria Piroddi, Emanuela Azara, Stefania Contini, and Emma Fenude. "Regioselective reductive electrophilic substitution of derivatives of 3,4,5-trimethoxybenzaldehyde." Journal of Organic Chemistry 57, no. 11 (May 1992): 3101–6. http://dx.doi.org/10.1021/jo00037a029.

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7

Frogley, Benjamin J., Andrew F. Dalebrook, and L. James Wright. "Regioselective Nitration and/or Halogenation of Iridabenzofurans through Electrophilic Substitution." Organometallics 35, no. 3 (January 27, 2016): 400–409. http://dx.doi.org/10.1021/acs.organomet.5b00981.

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8

Leitch, Sarah, Jennifer Addison-Jones, and Adam McCluskey. "Regioselective N- and C2-electrophilic substitution of 3-substituted indoles." Tetrahedron Letters 46, no. 16 (April 2005): 2915–18. http://dx.doi.org/10.1016/j.tetlet.2005.02.153.

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9

SMITH, K. "ChemInform Abstract: Highly Regioselective, Lewis Acid-Free Electrophilic Aromatic Substitution." ChemInform 28, no. 31 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199731235.

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10

Berthelot, Jacques, Catherine Guette, Paul-Louis Desbène, Jean-Jacques Basselier, Patrick Chaquin, and Daniel Masure. "Bromation régiosélective en série aromatique. I: Monobromation en position para de phénols et d'aminés aromatiques par le tribromure de tétrabutylammonium." Canadian Journal of Chemistry 67, no. 12 (December 1, 1989): 2061–66. http://dx.doi.org/10.1139/v89-320.

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The reaction of tetrabutylammonium tribromide (TBABr3) with phenols and aromatic amines in aprotic and non-basic solvents at 20 °C gives exclusively the corresponding para-brominated compounds in high yields. A mechanism involving electrophilic substitution by the tribromide anion Br3− itself is suggested to account for the results, especially the regioselective para bromination. Keywords: bromination, tetrabutylammonium tribromide, phenols, aromatic amines.

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11

Clark, George R., Paul M. Johns, Warren R. Roper, Tilo Söhnel, and L. James Wright. "Regioselective Mono-, Di-, and Trifunctionalization of Iridabenzofurans through Electrophilic Substitution Reactions." Organometallics 30, no. 1 (January 10, 2011): 129–38. http://dx.doi.org/10.1021/om100888z.

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12

Wallner, Olov A., and Kálmán J. Szabó. "Regioselective Palladium-Catalyzed Electrophilic Allylic Substitution in the Presence of Hexamethylditin." Organic Letters 4, no. 9 (May 2002): 1563–66. http://dx.doi.org/10.1021/ol0257777.

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13

AZZENA, U., G. MELLONI, A. M. PIRODDI, E. AZARA, S. CONTINI, and E. FENUDE. "ChemInform Abstract: Regioselective Reductive Electrophilic Substitution of Derivatives of 3,4,5-Trimethoxybenzaldehyde." ChemInform 23, no. 45 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199245143.

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14

Huang, Shuai Shuai, Zhan Jiang Zheng, Yu Ming Cui, Zheng Xu, Ke Fang Yang, and Li Wen Xu. "Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam." Synthesis 51, no. 22 (August 22, 2019): 4249–52. http://dx.doi.org/10.1055/s-0039-1690617.

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A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from commercially available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C–O coupling to introduce the difluoroethoxy moiety and chloroxidation conditions to give the desired sulfonyl chloride.

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15

Smolobochkin, Andrey V., Almir S. Gazizov, Nazerke K. Otegen, Julia K. Voronina, Anna G. Strelnik, Aida I. Samigullina, Alexander R. Burilov, and Michail A. Pudovik. "Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones." Synthesis 52, no. 21 (June 10, 2020): 3263–71. http://dx.doi.org/10.1055/s-0040-1707864.

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Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

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16

Azzena, Ugo, Teresa Denurra, Giovanni Melloni, and Anna Maria Piroddi. "Regioselective reductive electrophilic substitution of 1,2,3-trimethoxybenzene and its 5-alkyl-substituted homologs." Journal of Organic Chemistry 55, no. 19 (September 1990): 5386–90. http://dx.doi.org/10.1021/jo00306a016.

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17

Wallner, Olov A., and Kalman J. Szabo. "ChemInform Abstract: Regioselective Palladium-Catalyzed Electrophilic Allylic Substitution in the Presence of Hexamethylditin." ChemInform 33, no. 37 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200237058.

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18

Salzbrunn, Stefan, Juergen Simon, G. K. Surya Prakash, Nicos A. Petasis, and George A. Olah. "ChemInform Abstract: Considered Electrophilic Aromatic Substitution. Part 66. Regioselective Nitration of Arylboronic Acids." ChemInform 32, no. 5 (January 30, 2001): no. http://dx.doi.org/10.1002/chin.200105075.

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19

Zhang, Min, Jinling Su, Yan Zhang, Mingren Chen, Weiming Li, Xuewei Qin, Yanping Xie, Lixiao Qin, and Shihua Huang. "A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source." Synlett 30, no. 05 (January 30, 2019): 630–34. http://dx.doi.org/10.1055/s-0037-1612080.

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A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX2 alone or with ZnX2) promoted halogenation with N-halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X+) by the coordination of copper or zinc with the N-halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

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20

Kuendig, E. P., V. Desobry, C. Grivet, B. Rudolph, and S. Spichiger. "Regioselective electrophilic substitution via lithiation and intramolecular arene exchange (haptotropic rearrangement) in (naphthalene)tricarbonylchromium." Organometallics 6, no. 6 (June 1987): 1173–80. http://dx.doi.org/10.1021/om00149a007.

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21

H. Dodd, Robert, and Jean-François Rousseau. "Regioselective ortho-Directed Metalation and Electrophilic Substitution of Indole- and Indoline-5-(N-phenyl)carboxamides." HETEROCYCLES 55, no. 12 (2001): 2289. http://dx.doi.org/10.3987/com-01-9320.

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22

Vorontsova, Natalia V., Evgenii V. Vorontsov, Elena V. Sergeeva, and Valeria I. Rozenberg. "The first regioselective double electrophilic substitution of the C2-symmetric pseudo-meta-disubstituted [2.2]paracyclophanes." Tetrahedron Letters 47, no. 14 (April 2006): 2357–60. http://dx.doi.org/10.1016/j.tetlet.2006.02.003.

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23

AZZENA, U., T. DENURRA, G. MELLONI, and A. M. PIRODDI. "ChemInform Abstract: Regioselective Reductive Electrophilic Substitution of 1,2,3- Trimethoxybenzene and Its 5-Alkyl-Substituted Homologues." ChemInform 22, no. 10 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199110052.

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24

Rakowski DuBois, M., Lisa D. Vasquez, L. Peslherbe, and B. C. Noll. "Regioselective Electrophilic Substitution and Addition Reactions at an N-Coordinated Pyrrolyl Ligand in (PMe2Ph)3Cl2Re(NC4H4)." Organometallics 18, no. 11 (May 1999): 2230–40. http://dx.doi.org/10.1021/om9900216.

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25

Liu, Mengran, Marcin Ptaszek, Olga Mass, Daniel F. Minkler, Roger D. Sommer, Jayeeta Bhaumik, and Jonathan S. Lindsey. "Regioselective β-pyrrolic electrophilic substitution of hydrodipyrrin–dialkylboron complexes facilitates access to synthetic models for chlorophyll f." New Journal of Chemistry 38, no. 4 (2014): 1717. http://dx.doi.org/10.1039/c3nj01508d.

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26

Rousseau, Jean-Francois, and Robert H. Dodd. "ChemInform Abstract: Regioselective ortho-Directed Metalation and Electrophilic Substitution of Indole- and Indoline-5-(N-phenyl)carboxamides." ChemInform 33, no. 16 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200216135.

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27

Ibrahim, Dhuaou, Pascal Boulet, Philippe C. Gros, and Philippe Pierrat. "Efficient Access to Arylated Aza‐ullazines by Regioselective Functionalization of their Pyridine Ring by H−Li Exchange and Electrophilic Substitution." European Journal of Organic Chemistry 2021, no. 22 (June 14, 2021): 3331–39. http://dx.doi.org/10.1002/ejoc.202100333.

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28

Fixler, N., M. Demeunynck, and J. Lhomme. "Regioselective Electrophilic Substitution of 2-Hydroxy and 2-Methoxy Substituted Acridines. Application to the Synthesis of Pyrido[2,3,4-mn]acridine." Synthetic Communications 27, no. 13 (July 1997): 2311–24. http://dx.doi.org/10.1080/00397919708003387.

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29

Agarwal, Piyush K., Mohammad Saifuddin, and Bijoy Kundu. "Regioselective intramolecular electrophilic substitution reactions involving π-deficient pyridine substrates: a new entry to pyridoquinazolines and benzo[h][1,6]naphthyridines." Tetrahedron 66, no. 4 (January 2010): 862–70. http://dx.doi.org/10.1016/j.tet.2009.11.115.

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30

Vorontsova, Natalia V, Valeria I Rozenberg, Elena V Sergeeva, Evgenii V Vorontsov, Zoya A Starikova, Konstantin A Lyssenko, and Henning Hopf. "Symmetrically Tetrasubstituted [2.2]Paracyclophanes: Their Systematization and Regioselective Synthesis of Several Types of Bis-Bifunctional Derivatives by Double Electrophilic Substitution." Chemistry - A European Journal 14, no. 15 (May 19, 2008): 4600–4617. http://dx.doi.org/10.1002/chem.200701683.

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31

Fujita, Morifumi, Makoto Oshima, Sakuro Okuno, Takashi Sugimura, and Tadashi Okuyama. "Regioselective Reactions of 1-Alkylidene-2-oxyallyl Cations with Furan: Control of [4 + 3] Cycloaddition, [3 + 2] Cycloaddition, and Electrophilic Substitution." Organic Letters 8, no. 18 (August 2006): 4113–16. http://dx.doi.org/10.1021/ol061655t.

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32

Weber, Roland, Till Kühn, Hanspaul Hagenmaier, and Günter Häfelinger. "ab initio MO Optimization of Molecular Structures of Fluoro- and Chloro-Substituted Dibenzo-p-dioxines and the Effect of Halogen Substitution at the 2,3,7,8-Positions on Metabolic Attack." Zeitschrift für Naturforschung B 52, no. 11 (November 1, 1997): 1418–31. http://dx.doi.org/10.1515/znb-1997-1121.

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Full ab initio optimizations were performed on the molecular structures of 24 fluorinated and chlorinated dibenzodioxines (PFDD/PCDD ) and dibenzofurans (PFDF/PCDF). Reasonable agreement was found by comparing the geometries of four calculated structures with known X-ray data from the literature. For the fluorine substituent, calculated electron densities (Mulliken total charges and π-electron charges) clearly demonstrate the opposite influence of the inductive (I) and mesomeric (M) effect. The changes in π-densities at carbons in ortho-, meta- and para-position are constant for each fluorine substituent (independent of degree, pattern, and position of substitution). It is thus possible to calculate the π-densities of the substituted dioxines by increments starting from dibenzodioxine. π-Charges from quantum mechanical calculations and the increment system show good agreement even for OctaFDD (O8FDD ), where eight substituent effects are acting additively. Compared with fluorine, the chlorine substituent exercises a smaller -I-effect and a clearly weaker +M-effect. The HOMO coefficients of the unsubstituted dibenzodioxine and dibenzofuran, extracted from ab initio calculations, yield a good explanation for the observed regioselective metabolic attack at the 2,3,7,8-positions. The squares of the HOMO-coefficients of the 2,3,7,8-positions in dibenzodioxine (DD ) are about ten times greater than those of the 1,4,6,9-positions. These HOMO coefficients are practically unaffected by halide substitution. But halogen substitution reduces strongly the electron density at the halogen-bound carbon, which, however, is a necessary prerequisite for the electrophilic oxygen transfer during metabolism. One would therefore expect halogen substitution of dibenzodioxine and dibenzofuran (DF) at the 2,3,7,8-position to hinder metabolism, as is indeed found. This provides a plausible explanation for the highly selective tissue retention of 2,3,7,8-substituted PCDDs and PCDFs. Our ab initio calculations of five tetra CDDs (T4CDDs) confirm the postulate of Kobayashi et al. [1 ] who, using semiempirical calculations, found a correlation between the toxicity of a dioxine congener and its absolute molecular hardness. The 2,3,7,8-T4CDD also exhibits the smallest absolute hardness (derived from the HOMO-LUMO energy gap) in our calculations.

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33

FIXLER, N., M. DEMEUNYNCK, and J. LHOMME. "ChemInform Abstract: Regioselective Electrophilic Substitution of 2-Hydroxy- and 2-Methoxy- Substituted Acridines. Application to the Synthesis of Pyrido(2,3,4-mn) acridine." ChemInform 28, no. 37 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199737169.

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34

Agarwal, Piyush K., Mohammad Saifuddin, and Bijoy Kundu. "ChemInform Abstract: Regioselective Intramolecular Electrophilic Substitution Reactions Involving π-Deficient Pyridine Substrates: A New Entry to Pyridoquinazolines and Benzo[h][1,6]naphthyridines." ChemInform 41, no. 22 (June 1, 2010): no. http://dx.doi.org/10.1002/chin.201022142.

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35

Valle, Marcelo Siqueira, Aurélie Tarrade-Matha, Philippe Dauban, and Robert H. Dodd. "Regioselective electrophilic substitution of 2,3-aziridino-γ-lactones: preliminary studies aimed at the synthesis of α,α-disubstituted α- or β-amino acids." Tetrahedron 64, no. 2 (January 2008): 419–32. http://dx.doi.org/10.1016/j.tet.2007.10.082.

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36

Moghazy, Yasmen M., Nagwa MM Hamada, Magda F. Fathalla, Yasser R. Elmarassi, Ezzat A. Hamed, and Mohamed A. El-Atawy. "Understanding the reaction mechanism of the regioselective piperidinolysis of aryl 1-(2,4-dinitronaphthyl) ethers in DMSO: Kinetic and DFT studies." Progress in Reaction Kinetics and Mechanism 46 (January 2021): 146867832110274. http://dx.doi.org/10.1177/14686783211027446.

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Reactions of aryl 1-(2,4-dinitronaphthyl) ethers with piperidine in dimethyl sulfoxide at 25oC resulted in substitution of the aryloxy group at the ipso carbon atom. The reaction was measured spectrophotochemically and the kinetic studies suggested that the titled reaction is accurately third order. The mechanism is began by fast nucleophilic attack of piperidine on C1 to form zwitterion intermediate (I) followed by deprotonation of zwitterion intermediate (I) to the Meisenheimer ion (II) in a slow step, that is, SB catalysis. The regular variation of activation parameters suggested that the reaction proceeded through a common mechanism. The Hammett equation using reaction constant σo values and Brønsted coefficient value showed that the reaction is poorly dependent on aryloxy substituent and the reaction was significantly associative and Meisenheimer intermediate-like. The mechanism of piperidinolysis has been theoretically investigated using density functional theory method using B3LYP/6-311G(d,p) computational level. The combination between experimental and computational studies predicts what mechanism is followed either through uncatalyzed or catalyzed reaction pathways, that is, SB and SB-GA. The global parameters of the reactants, the proposed activated complexes, and the local Fukui function analysis explained that C1 carbon atom is the most electrophilic center of ether. Also, kinetics and theoretical calculation of activation energies indicated that the mechanism of the piperidinolysis passed through a two-step mechanism and the proton transfer process was the rate determining step.

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37

Jin, Li-Mei, Liang Chen, Juan-Juan Yin, Jin-Ming Zhou, Can-Cheng Guo, and Qing-Yun Chen. "Rational Synthesis ofmeso- or β- Fluoroalkylporphyrin Derivatives via Halo-fluoroalkylporphyrin Precursors: Electronic and Steric Effects on Regioselective Electrophilic Substitution in 5-Fluoroalkyl-10,20-diarylporphyrins." Journal of Organic Chemistry 71, no. 2 (January 2006): 527–36. http://dx.doi.org/10.1021/jo051672g.

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38

Gazizov, Almir S., Andrey V. Smolobochkin, Elizaveta A. Kuznetsova, Dinara S. Abdullaeva, Alexander R. Burilov, Michail A. Pudovik, Alexandra D. Voloshina, et al. "The Highly Regioselective Synthesis of Novel Imidazolidin-2-Ones via the Intramolecular Cyclization/Electrophilic Substitution of Urea Derivatives and the Evaluation of Their Anticancer Activity." Molecules 26, no. 15 (July 22, 2021): 4432. http://dx.doi.org/10.3390/molecules26154432.

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A series of novel 4-(het)arylimidazoldin-2-ones were obtained by the acid-catalyzed reaction of (2,2-diethoxyethyl)ureas with aromatic and heterocyclic C-nucleophiles. The proposed approach to substituted imidazolidinones benefits from excellent regioselectivity, readily available starting materials and a simple procedure. The regioselectivity of the reaction was rationalized by quantum chemistry calculations and control experiments. The anti-cancer activity of the obtained compounds was tested in vitro.

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39

Hirao, Seiya, Toshiki Yamashiro, Kyouka Kohira, Naoki Mishima, and Takumi Abe. "2,3-Dimethoxyindolines: a latent electrophile for SNAr reactions triggered by indium catalysts." Chemical Communications 56, no. 38 (2020): 5139–42. http://dx.doi.org/10.1039/d0cc01210f.

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40

Xue, Weichao, and Martin Oestreich. "Silicon Grignard Reagents as Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution." Synthesis 51, no. 01 (October 22, 2018): 233–39. http://dx.doi.org/10.1055/s-0037-1610309.

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A broad range of transition-metal catalysts is shown to promote allylic substitution reactions of allylic electrophiles with silicon Grignard reagents. The procedure was further elaborated for CuI as catalyst. The regioselectively is independent of the leaving group for primary allylic precursors, favoring α over γ. The stereochemical course of this allylic transposition was probed with a cyclic system, and anti-diastereoselectivity was obtained.

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41

Salman, Muhammad, Yaoyao Xu, Shahid Khan, Junjie Zhang, and Ajmal Khan. "Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications." Chemical Science 11, no. 21 (2020): 5481–86. http://dx.doi.org/10.1039/d0sc01763a.

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The first general example of Mo-catalyzed allylic sulfonylation of tertiary allylic electrophile provides an efficient way to forge sulfone moieties, and providing ample opportunities for further transformation through traditional Suzuki cross-coupling.

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42

Rao, K. Vara Prasad, and V. Sundaramurthy. "Regioselective electrophilic substitutions of 4H-imidazo[2,1-c][1,4]benzoxa(thia)zines." Journal of Organic Chemistry 57, no. 9 (April 1992): 2737–39. http://dx.doi.org/10.1021/jo00035a037.

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43

Cooper, Matthew A., and A. David Ward. "Cyclizations using Selenium Chemistry for Substituted 3-Hydroxypiperidines and 3-Hydroxypyrrolidines." Australian Journal of Chemistry 64, no. 10 (2011): 1327. http://dx.doi.org/10.1071/ch11073.

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The development of new methods for the stereoselective synthesis of nitrogen heterocycles is of current interest because of increasing demands for the syntheses of biologically important alkaloids and related compounds. It is shown that selenium-induced cyclization of 4-hydroxy-5-pentenylamines occurs regio- and stereo-selectively to afford cis-3-hydroxy-2-phenylselenomethylpyrrolidines, whereas 5-hydroxy-6-hexenylamines cyclize and give trans-3-hydroxy-2-phenylselenomethylpiperidines, with some compounds forming stable hydrates. In all cases cyclization proceeds regioselectively to give only the exo adducts with moderate to good diastereoselectivity. The reaction appeared to be under kinetic control as product ratios did not alter with time and the separated diastereomers did not interconvert when resubjected to the reaction conditions. These phenylseleno-substituted compounds could be transformed to diols by substitution of the corresponding selenone with a hydroxide ion. Substituted pyrrolidines and piperidines were thus afforded from unsaturated protected amines by electrophilic activation with SeII, followed by oxidation of the intermediate to SeVI and substitution with nucleophiles.

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44

Srinivas, Kolupula, Brice Kauffmann, Christel Dolain, Jean-Michel Léger, Léon Ghosez, and Ivan Huc. "Remote Substituent Effects and Regioselective Enhancement of Electrophilic Substitutions in Helical Aromatic Oligoamides." Journal of the American Chemical Society 130, no. 40 (October 8, 2008): 13210–11. http://dx.doi.org/10.1021/ja805178j.

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45

Tseng, Hsing-Chang, Arun Kumar Gupta, Bor-Cherng Hong, and Ju-Hsiou Liao. "Regioselective electrophilic substitutions of fulvenes with ethyl glyoxylate and subsequent Diels–Alder reactions." Tetrahedron 62, no. 7 (February 2006): 1425–32. http://dx.doi.org/10.1016/j.tet.2005.11.029.

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46

RAO, K. V. P., and V. SUNDARAMURTHY. "ChemInform Abstract: Regioselective Electrophilic Substitutions of 4H-Imidazo(2,1-c)(1,4)benzoxa(thia)zines." ChemInform 23, no. 41 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199241179.

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47

Dax, K., M. Albert, J. Ortner, and B. J. Paul. "Fluorinated Carbohydrates. Some New Aspects in Synthesis and Application." Current Organic Chemistry 3, no. 3 (May 1999): 287–307. http://dx.doi.org/10.2174/1385272803666220202194417.

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Abstract: Recent applications of glycosyl fluorides as donors in controlled di- and oligosaccharide synthesis employing chemical and enzymatic methods are presented. Within the chemical approaches significant contributions have been made by the development of fluorophilic activators displaying high stereoselectivity as well as further improvements in "reactivity fine tuning" by variation of protecting groups. In the field of enzymatic oligosaccharide synthesis progress has been made in regioselective glycosyl transfer to secondary hydroxyl groups. Additionally, promising new approaches employing fluorides derived from monosaccharides with specifically mutated glycosidases or disaccharide derived fluorides with cellulases, have been developed. From the numerous contributions regarding the synthesis of deoxy-fluoro aldoses, emphasis is placed upon side-reactions on attempted nucleophilic substitutions. Within this field modification of pentoses at C-2 using the sulfonate/fluoride route or applying diethylaminosulfur trifluoride are discussed. The increasing use of asymmetric synthesis in this field, including a new entry starting from a chiral cis-diol, is noteworthy. Scope and limitations in the synthesis of 2-deoxy-2-fluoro aldoses by electrophilic addition across the double bond of glycals by making use of the new class of N-F-fluorinating agents are presented. The important role of fluorinated carbohydrates as probes in mechanistic enzyme studies as well as their application in biomedical research is illustrated by several examples.

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Shravani, Madishetti, Shanigaram Balaiah, Kolupula Srinivas, K. Bhanuprakash, and Ivan Huc. "Unusual Regioselective Electrophilic Substitutions in Quinoline Foldamers: Conceptual DFT and Frontier Molecular Orbital Analysis Reveal the Crucial Role of Folding and Substituents." ChemPhysChem 13, no. 15 (August 7, 2012): 3526–34. http://dx.doi.org/10.1002/cphc.201200397.

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Smith, Keith, and Gamal A. El-Hiti. "Regioselective Control of Electrophilic Aromatic Substitution Reactions." ChemInform 36, no. 8 (February 22, 2005). http://dx.doi.org/10.1002/chin.200508273.

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Smith, Keith, and Gamal A. El-Hiti. "Regioselective Electrophilic Aromatic Substitution Reactions over Reusable Zeolites." ChemInform 38, no. 2 (January 9, 2007). http://dx.doi.org/10.1002/chin.200702238.

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