Relevant bibliographies by topics / Regioselective electrophilic substitution

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  1. Journal articles
  2. Dissertations / Theses

Academic literature on the topic 'Regioselective electrophilic substitution'

Author: Grafiati
Published: 9 March 2023

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Journal articles on the topic "Regioselective electrophilic substitution"

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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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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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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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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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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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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Dissertations / Theses on the topic "Regioselective electrophilic substitution"

1

Roberts, S. D. "Regioselective electrophilic aromatic substitution reactions of naphthalene over solids." Thesis, Swansea University, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.638685.

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Chapter 1 highlights the many advantages of heterogeneous inorganic solids as catalysts, and summarises the various microporous and mesoporous solids that have been employed as catalysts. The synthesis and characterisation of the mesoporous materials that were used in the study are described. Chapter 2 focuses on the nitration of naphthalene. An introduction to nitration is given, and the results of nitration over a range of solids are presented. Unusual dinitronaphthalene product ratios were achieved over Al-MCM-41. Reactions catalysed by heteropoly acid immobilised within the pores of mesoporous materials are also described. Chapters 3 to 6 focus upon the alkylation of naphthalene. Emphasis is placed upon the importance of 2,6-dialkylnaphthalenes (2,6-DAN) as intermediates for the production of high performance engineering plastics, and why there is still significant room for improvement in both 2,6-DAN yield and selectivity. A molecular modelling study of 2,6- and 2,7- di-tert-butylnaphthalene (DTBN) highlighted the potential for achieving selectivity for the 2,6-over the 2,7-isomer. Zeolite H-Mordenite (HM) was the most selective catalyst for 2,6-DTBN, but showed poor activity. Efforts to increase both the 2,6-DTBN yield and selectivity over HM focused upon varying the reaction time; temperature; pressure; solvent; amount of alkylating agent, solvent, and catalyst; Si/Al ratio of the catalyst; and mode of addition. Optimisation resulted in a 60% yield of 2,6-DTBN with a 2,6/2,7 ratio of over 50. tert-Butylation reactions were achieved using mainly tert-butanol as the alkylating agent. The identification of by-products in the tert-butylation reaction has been attempted. Alkylation with other alkylating agents has been attempted, but selectivity for 2,6-DAN was inferior to that achieved in the tert-butylation reaction using tert-butanol.
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2

Calogero, F. "NEW SYNTHETIC PROCESSES FOR THE APIS INDUSTRIAL PRODUCTION: THE CASE OF SILODOSIN." Doctoral thesis, Università degli Studi di Milano, 2014. http://hdl.handle.net/2434/243613.

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This thesis is focused on the development of new synthetic processes for the production of already known Active Pharmaceutical Ingredients (APIs). The research work was performed in the laboratories of Dipharma Francis srl, a company which operates in the generic drug market. The launch of the generic version of a drug in the market often leads to lowering of product prices for both the branded product and the generic ones. For this reason, the process adopted to produce an API has to be innovative, efficient, safe and, of course, cheaper than the existing ones, in order to be competitive in the market. During my Ph.D. I worked on the synthesis of some APIs, in particular here I report the feasibility and development studies of an alternative process to produce silodosin. Silodosin is an API used as a treatment for the symptoms of Benign Prostatic Hyperplasia (BPH). In order to establish the synthetic strategy and to outline our freedom to operate, an accurate survey of the whole patent literature about silodosin has been done. During the feasibility study several synthetic approaches have been tried in order to functionalise indoline at positions 5 and 7. A copper(I) catalysed C-arylation reaction and a regioselective electrophilic aromatic substitution revealed to be the best choices to introduce respectively substituents in position 5 and 7 of indoline. The synthesis continued with a diastereoselective reductive amination which after crystallisation yielded optically pure amine intermediate that is the key intermediate for the synthesis of silodosin and ended converting amine intermediate into Silodosin using already reported procedures. Our new process to prepare silodosin starting from commercially available and cheap indoline consists of 11 steps. The whole synthetic route has been performed in gram scale using only 4 purifications of key intermediates. Silodosin has been finally obtained in a 10% overall yield, with a purity greater than 99% measured by HPLC and an optical purity greater than 99% measured by HPLC on chiral stationary phase.
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3

Sayah, Ghassemi Babak. "Chimie et réactivité des hexahydropyrroloindolizines : application à la synthèse des myrmicarines." Université Joseph Fourier (Grenoble), 2001. http://www.theses.fr/2001GRE10114.

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Parmi les composes naturels ou synthetiques possedant des activites biologiques interessantes, les alcaloides tiennent une part importante. Recemment une nouvelle famille d'alcaloides bicycliques et oligocycliques, nommee myrmicarine, a ete isolee de glandes a poisons de fourmis d'afrique de type mirmicinae. La plupart de ces composes possedent en totalite ou en partie un motif hexahydropyrroloindolizine contenant un centre stereogene dont la configuration absolue n'est pas connue. Nous avons entrepris la synthese de ces alcaloides sous forme enantiopure. Dans un premier temps, suivant une strategie divergente basee sur des reactions de substitution electrophile regioselective sur un noyau pyrrolique nous avons synthetise un motif hexahydropyrroloindolizinone sous forme enantiopure, et par la suite les myrmicarines 217 et 215 (a et b). Dans un deuxieme temps, nous avons etudie la regioselectivite des reactions d'acylation de type vilsmeier-haack sur le tricycle quasi-symetrique hexahydropyrroloindolizine. Des conditions ideales ont ete mises au point permettant une substitution electrophile regiospecifique. Cette etude a ouvert une deuxieme voie d'acces aux myrmicarines 217 et 215 (a et b). Enfin nous avons propose deux voies d'acces a la myrmicarine 430 dont une est basee sur l'auto condensation des myrmicarines 215 (a et b) et pourrait etre assimilee a une synthese biomimetique de cet alcaloide.
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Tseng, Hsin-chang, and 曾信彰. "I. Regioselective Electrophilic Substitutions of Fulvenes with Ethyl Glyoxylate II. Organocatalytic Cycloaddition of ?β-Unsaturated Carbonyl Compounds." Thesis, 2007. http://ndltd.ncl.edu.tw/handle/22376898508086793225.

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Abstract:
博士
國立中正大學
化學所
95
Part I: Regioselective Electrophilic Substitutions of Fulvenes with Ethyl glyoxalate. Highly regioselective electrophilic substitution of fulvenes with ethyl glyoxylate, catalyzed by EtAlCl2 or Yb(OTf)3 was achieved. Subsequent Diels–Alder reaction of the adduct with various dienophiles provides an efficient protocol toward highly functionalized indane and tricyclo[5.2.1.02,6]dec-8-ene systems. Part II: Organocatalytic Cycloaddition of ?β-Unsaturated Carbonyl compounds The highly enantioselective organocatalyzed [3 + 3] and [4 + 2] cycloaddition of ?β-unsaturated carbonyl compounds is reported. The methodology was used in the synthesis of (-)-isopulegolhydrate, (-)-cubebaol, polysubstitued aromatic aldehydes. In addition organocatalytic intermolecular cycloaddition of glutaric dialdehyde and methyl vinyl ketone is reported. The methodology was also used in the synthesis of (+)-palitantine.
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