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Journal articles on the topic 'Aliphatic nucleophilic substitution'

Author: Grafiati

Published: 24 April 2022

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1

Christoffers, Jens, and Mathias S. Wickleder. "Synthesis of Aromatic and Aliphatic Di-, Tri-, and Tetrasulfonic Acids." Synlett 31, no. 10 (2020): 945–52. http://dx.doi.org/10.1055/s-0039-1691745.

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Oligosulfonic acids are promising linker compounds for coordination polymers and metal-organic frameworks, however, compared to their carboxylic acid congeners, often not readily accessible by established synthetic routes. This Account highlights the synthesis of recently developed aromatic and aliphatic di-, tri- and tetrasulfonic acids. While multiple electrophilic sulfonations of aromatic substrates are rather limited, the nucleophilic aromatic substitution including an intramolecular variant, the Newman–Kwart rearrangement, allows the flexible introduction of up to four sulfur-containing m

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2

SHORTER, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution." ChemInform 22, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199135300.

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3

SHORTER, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution." ChemInform 26, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199536314.

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4

Shorter, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution." ChemInform 33, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.200250265.

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5

SHORTER, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution." ChemInform 24, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199302305.

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6

Shorter, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution." ChemInform 31, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.200016307.

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7

Lund, Henning, Kim Daasbjerg, Torben Lund, and Steen U. Pedersen. "On Electron Transfer in Aliphatic Nucleophilic Substitution." Accounts of Chemical Research 28, no. 7 (1995): 313–19. http://dx.doi.org/10.1021/ar00055a005.

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8

Abramov, Michael A., Suzanne Toppet, and Wim Dehaen. "Regiospecific Nucleophilic Substitution of Fluorine in Fused Tetrafluoroquinolines with N- and O-Nucleophiles." Journal of Chemical Research 2002, no. 8 (2002): 357–58. http://dx.doi.org/10.3184/030823402103172455.

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5,6,7,8-Tetrafluoro-1,2-azolo[3,4- b;4′,3′- e]quinolines react regiospecifically with aliphatic and aromatic amines, alcohols and phenols yielding 7-substituted 5,6,8-trifluoro-1,2-azolo[3,4- b;4′,3′- e]quinolines.

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9

SHORTER, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199145328.

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10

Katritzky, Alan R., and Bogumil E. Brycki. "The mechanisms of nucleophilic substitution in aliphatic compounds." Chemical Society Reviews 19, no. 2 (1990): 83. http://dx.doi.org/10.1039/cs9901900083.

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11

Jaiswal, Amit K., Pragati K. Prasad, and Rowan D. Young. "Nucleophilic Substitution of Aliphatic Fluorides via Pseudohalide Intermediates." Chemistry – A European Journal 25, no. 25 (2019): 6290–94. http://dx.doi.org/10.1002/chem.201806272.

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12

SHORTER, J. "ChemInform Abstract: Nucleophilic Aliphatic Substitution (Organic Reaction Mechanisms)." ChemInform 25, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199418286.

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13

LUND, H., K. DAASBJERG, T. LUND, and S. U. PEDERSEN. "ChemInform Abstract: Electron Transfer in Aliphatic Nucleophilic Substitution." ChemInform 26, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199544298.

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14

Li, Feiming, Fangyuan Lin, Yipeng Huang, et al. "Bromobenzene aliphatic nucleophilic substitution guided controllable and reproducible synthesis of high quality cesium lead bromide perovskite nanocrystals." Inorganic Chemistry Frontiers 6, no. 12 (2019): 3577–82. http://dx.doi.org/10.1039/c9qi01095e.

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We develop a new chemical design for the controllable and reproducible synthesis of high quality CsPbBr<sub>3</sub> perovskite nanocrystals in one step based on bromobenzene and alkane amine aliphatic nucleophilic substitution.

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15

LUND, H. "ChemInform Abstract: Single Electron Transfer in Aliphatic Nucleophilic Substitution." ChemInform 22, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199137289.

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16

Ono, Noboru, Tetsuya Yanai, Akio Kamimura, and Aritsune Kaji. "Lewis acid-induced nucleophilic substitution reactions of aliphatic nitro compounds with carbon nucleophiles." Journal of the Chemical Society, Chemical Communications, no. 16 (1986): 1285. http://dx.doi.org/10.1039/c39860001285.

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17

Shinde, Sandip S., and Sunil N. Patil. "One molecule of ionic liquid and tert-alcohol on a polystyrene-support as catalysts for efficient nucleophilic substitution including fluorination." Org. Biomol. Chem. 12, no. 45 (2014): 9264–71. http://dx.doi.org/10.1039/c4ob01781a.

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The tert-alcohol and ionic liquid solvents in one molecule [mim-<sup>t</sup>OH][OMs] was immobilized on polystyrene and reported to be a highly efficient catalyst in aliphatic nucleophilic substitution using alkali metal salts.

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18

Šafář, Peter, and Jaroslav Kováč. "Preparation of unsymmetrically substituted Stenhouse salts." Collection of Czechoslovak Chemical Communications 54, no. 9 (1989): 2425–32. http://dx.doi.org/10.1135/cccc19892425.

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Unsymmetrically substituted Stenhouse salts IVa-IVj (iminium salts of 1-phenylmethylamino-5-(4-X-phenylamino)-2-hydroxy-2,4-pentadienal) arise by reaction of N-2-furfurylidene-N-phenylmethyliminium perchlorate (V) with substituted anilines. Primary and secondary aliphatic amines do not react in this way. Unsymmetrically substituted Stenhouse salts are also formed from iminium salt of 1,5-di(phenylmethylamino)-2-acetoxy-2,4-pentadienal (IV) by nucleophilic substitution with aromatic and aliphatic amines.

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19

Daasbjerg, Kim, Steen U. Pedersen, Henning Lund, K. P. J. O'Reilly, Anne Ertan, and Erich Kleinpeter. "On the Occurrence of Electron Transfer in Aliphatic Nucleophilic Substitution." Acta Chemica Scandinavica 45 (1991): 424–30. http://dx.doi.org/10.3891/acta.chem.scand.45-0424.

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20

ROSSI, R. A., and A. N. SANTIAGO. "ChemInform Abstract: Electron Transfer in Aliphatic Radical Nucleophilic Substitution Reactions." ChemInform 26, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199520288.

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21

Dawane, Bhaskar, Shuddhodan Kadam, Ajay Ambhore, et al. "Metal-Free One-Pot Chemoselective Thiocyanation of Imidazothiazoles and 2-Aminothiazoles with in situ Generated N-Thiocyanatosuccinimide." Synlett 29, no. 14 (2018): 1902–8. http://dx.doi.org/10.1055/s-0037-1609553.

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A chemoselective thiocyanation of imidazothiazoles and 2-aminothiazoles with use of in situ generated N-thiocyanatosuccinimide (NTS) at room temperature is described. The protocol offers mild reaction conditions and high chemoselectivity for electrophilic substitution in imidazothiazoles over nucleophilic substitution. This method provides metal-free and easy conversion of imidazothiazoles and 2-aminothiazoles into their corresponding C-3 and C-5 thiocyanates, respectively, in good to excellent yield. The present protocol also offers the effective thiocyanation of bifunctional imidazothiazoles

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22

Lund, Torben, Henning Lund, J. Chattopadhyaya, Li-An Lu, Pui-Fun Louisa Tang, and Anders Ljungqvist. "Single Electron Transfer as Rate-Determining Step in an Aliphatic Nucleophilic Substitution." Acta Chemica Scandinavica 40b (1986): 470–85. http://dx.doi.org/10.3891/acta.chem.scand.40b-0470.

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23

Lund, Torben, and Henning Lund. "Single electron-transfer as rate-determining step in an aliphatic nucleophilic substitution." Tetrahedron Letters 27, no. 1 (1986): 95–98. http://dx.doi.org/10.1016/s0040-4039(00)83950-7.

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24

Lund, Torben. "Correlation between inner-sphere stabilization and stereochemistry for the aliphatic nucleophilic substitution." Tetrahedron Letters 32, no. 12 (1991): 1595–98. http://dx.doi.org/10.1016/s0040-4039(00)74281-x.

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25

Ji, Pengju, John Atherton, and Michael I. Page. "Liquid Ammonia as a Dipolar Aprotic Solvent for Aliphatic Nucleophilic Substitution Reactions." Journal of Organic Chemistry 76, no. 5 (2011): 1425–35. http://dx.doi.org/10.1021/jo102173k.

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26

Banfi, Luca, Renata Riva, and Andrea Basso. "Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes." Synlett 2010, no. 01 (2009): 23–41. http://dx.doi.org/10.1055/s-0029-1218527.

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27

Ranyuk, Elena, Hasrat Ali, Brigitte Guérin, and Johan E. van Lier. "A new approach for the synthesis of 18F-radiolabelled phthalocyanines and porphyrins as potential bimodal/theranostic agents." Journal of Porphyrins and Phthalocyanines 17, no. 08n09 (2013): 850–56. http://dx.doi.org/10.1142/s1088424613500545.

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The synthesis of a series of new fluorinated phthalocyanines and porphyrins as potential bimodal probes is evaluated. In these complexes, zinc phthalocyanine functions as a fluorescence imaging moiety while attachment of an aliphatic chain of different lengths bearing a tosylate group permits introduction of fluorine via nucleophilic substitution of the tosylate group. Using short-lived [18F]fluoride gives the analogous 18 F -radiolabelled tracer rendering the bimodal probe suitable for both fluorescence and PET imaging.

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28

Döring, Thomas, Romesh C. Boruah, and Wolfgang Pfleiderer. "Synthesis of 7-Acyl-2,4-disubstituted Pteridines by Radical Nucleophilic Substitution and Displacement Reactions." Pteridines 15, no. 4 (2004): 129–48. http://dx.doi.org/10.1515/pteridines.2004.15.4.129.

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Abstract 2,4-Disubstituted pteridine derivatives (1-3) react with acyl radicals very selectively in position 7 by a nucleophilic Substitution mechanism (4-10). Oxidation of the 2-methylthio group proceeds with m-chloroperbenzoic acid in good yields to the corresponding 7-acyl-2-methylsulfonyl-4-aminopteridines (11-16). The methylsulfonyl group can easily been displaced by nucleophiles such as aliphatic amines (27, 29, 32-42, 45), cyclic amines (56-61), aromatic amines (30, 31) and amino acids (43-54). Oxygen nucleophiles lead to 7-acyl-isopterin derivatives (62-66). The acyl side-chain is also

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29

Navarro, Rodrigo, Mónica Pérez, Gema Rodriguez, and Helmut Reinecke. "Selective nucleophilic substitution reactions on poly(epichlorohydrin) using aromatic and aliphatic thiol compounds." European Polymer Journal 43, no. 10 (2007): 4516–22. http://dx.doi.org/10.1016/j.eurpolymj.2007.07.033.

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30

Chugunova, Elena, Vincenzo Frenna, Giovanni Consiglio, et al. "On the Nucleophilic Reactivity of 4,6-Dichloro-5-nitrobenzofuroxan with Some Aliphatic and Aromatic Amines: Selective Nucleophilic Substitution." Journal of Organic Chemistry 85, no. 21 (2020): 13472–80. http://dx.doi.org/10.1021/acs.joc.0c01502.

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31

Chiacchiera, Stella M., Joaqu�n O. Singh, Jorge D. Anunziata, and Juana J. Silber. "Aromatic nucleophilic substitution reactions of 1,2-dinitrobenzene with aliphatic primary amines in n-hexane; catalysis by non-nucleophilic bases." Journal of the Chemical Society, Perkin Transactions 2, no. 8 (1987): 987. http://dx.doi.org/10.1039/p29870000987.

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32

Lund, Torben, Karin Bay Jacobsen, Carsten Christophersen, et al. "Complete Inversion of Configuration in Aliphatic Nucleophilic Substitution Reactions with Small Inner-Sphere Stabilization." Acta Chemica Scandinavica 52 (1998): 778–83. http://dx.doi.org/10.3891/acta.chem.scand.52-0778.

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33

Oestreich, Martin, and Jonas Scharfbier. "Copper-Catalyzed Si–B Bond Activation in the Nucleophilic Substitution of Primary Aliphatic Triflates." Synlett 27, no. 08 (2016): 1274–76. http://dx.doi.org/10.1055/s-0035-1561407.

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34

Okhlobystina, Aleksandra V., Andrey O. Okhlobystin, Nadezhda T. Berberova, and Daria A. Burmistrova. "HYDROGEN SULFIDE AND ALKANTHIOLS IN NUCLEOPHILIC SUBSTITUTION REACTIONS OF HYDROXY GROUPS IN ALIPHATIC ALCOHOLS." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 62, no. 8 (2019): 61–65. http://dx.doi.org/10.6060/ivkkt.20196208.5889.

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Hydrogen sulfide and alkanethiols are toxic compounds containing in the production of wells in many oil and gas condensate fields. Because the policy of hydrocarbon processing enterprises aimed at the development of new fundamental research, processes and technologies in order to find rational use of raw materials, the conversion of hydrogen sulfide and alkanethiols into valuable compounds is one of the strategic goals of the oil and gas industry. The methods of "green" chemistry are perspective processes for converting hydrogen sulfide and alkantiols into valuable organic compounds, which all

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35

Block, Dirk, Bernd Klatte, Arndt Knöchel, Rainer Beckmann, and Uwe Holm. "N.C.A. [18F]-labelling of aliphatic compounds in high yields via aminopolyether - supported nucleophilic substitution." Journal of Labelled Compounds and Radiopharmaceuticals 23, no. 5 (1986): 467–77. http://dx.doi.org/10.1002/jlcr.2580230503.

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36

Al-Khalil, Suleiman I., W. Russell Bowman, Katherine Gaitonde, Madeleine A. Marley (née Nagel) та Geoffrey D. Richardson. "Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds." Journal of the Chemical Society, Perkin Transactions 2, № 9 (2001): 1557–65. http://dx.doi.org/10.1039/b103350f.

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37

Martinez, Henry, Adele Rebeyrol, Taylor B. Nelms та William R. Dolbier. "Impact of fluorine substituents on the rates of nucleophilic aliphatic substitution and β-elimination". Journal of Fluorine Chemistry 135 (березень 2012): 167–75. http://dx.doi.org/10.1016/j.jfluchem.2011.10.008.

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38

Loch, A. R., K. A. Lippa, D. L. Carlson, Y. P. Chin, S. J. Traina, and A. L. Roberts. "Nucleophilic Aliphatic Substitution Reactions of Propachlor, Alachlor, and Metolachlor with Bisulfide (HS-) and Polysulfides (Sn2-)." Environmental Science & Technology 36, no. 19 (2002): 4065–73. http://dx.doi.org/10.1021/es0206285.

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39

Saputra, Mirza A., Rashel L. Forgey, Jeffrey L. Henry, and Rendy Kartika. "Mechanistic insights into Brønsted acid-induced nucleophilic substitution of aliphatic imidazole carbamate with halide ions." Tetrahedron Letters 56, no. 11 (2015): 1392–96. http://dx.doi.org/10.1016/j.tetlet.2015.01.098.

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40

CHIRIAC, C. I., M. SAVA, M. TIBIRNA, et al. "ChemInform Abstract: Aromatic Nucleophilic Substitution Reactions of 2,4- Dinitrobenzenesulfonic Acid Sodium-Salt with Aliphatic Amides." ChemInform 27, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199636081.

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41

Shi, Weimin, Jingjie Zhang, Fengqian Zhao, et al. "Nucleophilic Aromatic Substitution of Unactivated Aryl Fluorides with Primary Aliphatic Amines by Organic Photoredox Catalysis." Chemistry – A European Journal 26, no. 65 (2020): 14823–27. http://dx.doi.org/10.1002/chem.202002315.

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42

ESIKOVA, I. A. "ChemInform Abstract: Nucleophilic Aliphatic and Aromatic Substitution in Phase-Transfer Catalysis: Mechanisms and Synthetic Applications." ChemInform 28, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199745323.

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43

Jain, Ajay K., Vinod K. Gupta, and Anurag Kumar. "Aromatic nucleophilic substitution reactions of oxime ethers with aliphatic primary and secondary amines in benzene." Journal of the Chemical Society, Perkin Transactions 2, no. 1 (1990): 11. http://dx.doi.org/10.1039/p29900000011.

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44

Singh, Joaquín O., Jorge D. Anunziata та Juana J. Silber. "n–π Electron donor–acceptor complexes. II. Aliphatic amines with dinitrobenzenes". Canadian Journal of Chemistry 63, № 4 (1985): 903–7. http://dx.doi.org/10.1139/v85-150.

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The interaction of several aliphatic amines as n-donors and dinitrobenzenes (DNB) as π-acceptors has been studied in n-hexane. The formation of electron donor – acceptor (EDA) complexes is proposed to explain the spectroscopic behaviour of the mixtures. The stability constants (Ks) for these complexes have been calculated by an iterative procedure. For a given acceptor, the donor strength of RNH2 > R2NH > R3N was found. This order is explained by considering the role that steric effect may play in the EDA complex formation. On the other hand, the fact that for a given donor Ks follows th

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45

Tolbert, Laren M., Joanne Bedlek, Michael Terapane, and Janusz Kowalik. "Spectral Evidence for Single Electron Transfer in Nucleophilic Aliphatic Substitution of a Carbanion by Methyl Iodide." Journal of the American Chemical Society 119, no. 9 (1997): 2291–92. http://dx.doi.org/10.1021/ja9620402.

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46

Isanbor, Chukwuemeka, and Thomas A. Emokpae. "Nucleophilic heteroaromatic substitution: Kinetics of the reactions of nitropyridines with aliphatic amines in dipolar aprotic solvents." International Journal of Chemical Kinetics 40, no. 3 (2008): 125–35. http://dx.doi.org/10.1002/kin.20297.

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47

Ashby, E. C., Xiaojing Sun, and J. L. Duff. "Single Electron Transfer in Nucleophilic Aliphatic Substitution. Evidence for Single Electron Transfer in the Reactions of 1-Halonorbornanes with Various Nucleophiles." Journal of Organic Chemistry 59, no. 6 (1994): 1270–78. http://dx.doi.org/10.1021/jo00085a012.

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48

Motiwala, Hashim F., Raj Kumar, and Asit K. Chakraborti. "Microwave-Accelerated Solvent- and Catalyst-Free Synthesis of 4-Aminoaryl/alkyl-7-chloroquinolines and 2-Aminoaryl/alkylbenzothiazoles." Australian Journal of Chemistry 60, no. 5 (2007): 369. http://dx.doi.org/10.1071/ch06391.

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An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed. Thus, the treatment of 4,7-dichloroquinoline (1 equiv.) with a mixture of aniline (2 equiv.) and phenol (2 equiv.) afforded exclu

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49

Pross, Addy. "Limitations of the Reactivity-Selectivity Principle. Application to Free Radical Addition to Alkenes and Nucleophilic Aliphatic Substitution." Israel Journal of Chemistry 26, no. 4 (1985): 390–94. http://dx.doi.org/10.1002/ijch.198500125.

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50

Antony Savarimuthu, S., D. G. Leo Prakash, and S. Augustine Thomas. "Nucleophilic substitution of propargyl alcohols with aliphatic alcohols, aliphatic amines and heterocycles catalyzed by 4-nitrobenzenesulfonic acid: a scalable and metal-free process." Tetrahedron Letters 55, no. 21 (2014): 3213–17. http://dx.doi.org/10.1016/j.tetlet.2014.02.086.

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