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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 4
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Original Articles

Reductive Lithiation of Some Thioketals Using Lithium 1-(Dimethylamino)naphthalenide

Theodore Cohen Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, 15260, USA
&
James R. Matz Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, 15260, USA
Pages 311-317 | Published online: 06 Dec 2006

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Theodore Cohen. (1993) The Versatile Phenylthio Group. A Powerful Aid in Synthesis. Phosphorus, Sulfur, and Silicon and the Related Elements 74:1-4, pages 1-15.
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Articles from other publishers (64)

Hao Liang & James P. Morken. (2023) Substrate Plasticity Enables Group-Selective Transmetalation: Catalytic Stereospecific Cross-Couplings of Tertiary Boronic Esters. Journal of the American Chemical Society 145:38, pages 20755-20760.
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Zhonglin Tao, Kevin A. Robb, Jesse L. Panger & Scott E. Denmark. (2018) Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration. Journal of the American Chemical Society 140:46, pages 15621-15625.
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Zhonglin Tao, Kevin A. Robb, Kuo Zhao & Scott E. Denmark. (2018) Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes. Journal of the American Chemical Society 140:10, pages 3569-3573.
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Richard R. Hill & Scott D. Rychnovsky. (2016) Generation, Stability, and Utility of Lithium 4,4′-Di- tert -butylbiphenylide (LiDBB) . The Journal of Organic Chemistry 81:22, pages 10707-10714.
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K. Ramalingam, C. Rizzoli, G.S. Sivagurunathan, S. Sivasekar, T. Rajaraman & M. Prabu. (2016) Anhydrous Aluminum Chloride Catalyzed Methylene Group Inclusion: Mechanistic, Spectral and Single Crystal X-Ray Structural Study on Methanediyl Bis(Cyclohexylmethylcarbamodithioate). International Letters of Chemistry, Physics and Astronomy 68, pages 61-70.
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Nicole Kennedy, Peng Liu & Theodore Cohen. (2015) Fundamental Difference in Reductive Lithiations with Preformed Radical Anions versus Catalytic Aromatic Electron‐Transfer Agents: N , N‐ Dimethylaniline as an Advantageous Catalyst . Angewandte Chemie International Edition 55:1, pages 383-386.
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Nicole Kennedy, Peng Liu & Theodore Cohen. (2015) Fundamental Difference in Reductive Lithiations with Preformed Radical Anions versus Catalytic Aromatic Electron‐Transfer Agents: N , N‐ Dimethylaniline as an Advantageous Catalyst . Angewandte Chemie 128:1, pages 391-394.
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Nicole Kennedy, Gang Lu, Peng Liu & Theodore Cohen. (2015) Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent. The Journal of Organic Chemistry 80:17, pages 8571-8582.
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Mark D. Ferguson & Roman A. Ivanov. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 3 .
Matthew A. Perry & Scott D. Rychnovsky. (2015) Generation, structure and reactivity of tertiary organolithium reagents. Natural Product Reports 32:4, pages 517-533.
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J.M. Manthorpe, H.I. Kong, J.W. Palko & M.A. Gill. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 1031 1085 .
A. Krief & A. Kremer. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 56 156 .
James E. Biggs-Houck, Rebecca L. Davis, Jingqiang Wei, Brandon Q. Mercado, Marilyn M. Olmstead, Dean J. Tantillo & Jared T. Shaw. (2011) Carbon–Carbon Bond-Forming Reactions of α-Thioaryl Carbonyl Compounds for the Synthesis of Complex Heterocyclic Molecules. The Journal of Organic Chemistry 77:1, pages 160-172.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 683 687 .
Roman Ivanov, Ilan Marek & Theodore Cohen. (2010) The superiority of properly prepared lithium 1-N,N-dimethylaminonaphthalenide (LDMAN) over other aromatic radical-anions for the generation of organolithiums by reductive lithiation. Tetrahedron Letters 51:1, pages 174-176.
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Zvi RappoportCarmen Najera & Miguel Yus. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Louis Fieser & Janice Smith. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Ao Yang, Heather Butela, Kai Deng, Mary Dosch Doubleday & Theodore Cohen. (2006) Organolithiums by reductive lithiation: the catalytic aromatic method versus the use of preformed aromatic radical-anions. Naphthalene can behave as a catalyst or an inhibitor. Tetrahedron 62:27, pages 6526-6535.
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Kai Deng, Ahlem Bensari-Bouguerra, Joseph Whetstone & Theodore Cohen. (2006) Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums Prepared by the Action of Aromatic Radical Anions on Phenyl Thioethers. High Stereoselectivity in the Cyclization Accelerated by an Allylic Lithium Oxyanion 1 . The Journal of Organic Chemistry 71:6, pages 2360-2372.
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Stéphane Streiff, Nigel Ribeiro & Laurent Désaubry. (2004) Synthesis of Allylsilanes by Reductive Lithiation of Thioethers. The Journal of Organic Chemistry 69:22, pages 7592-7598.
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Jonathan Clayden. 2002. Organolithiums: Selectivity for Synthesis. Organolithiums: Selectivity for Synthesis 149 168 .
Mitsuru Shindo, Ryoko Koretsune, Wakako Yokota, Kotaro Itoh & Kozo Shishido. (2001) Practical synthesis of ynolate anions: naphthalene-catalyzed reductive lithiation of α,α-dibromo esters. Tetrahedron Letters 42:47, pages 8357-8360.
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Uko E. Udodong. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Alain Krief. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Mark D. Ferguson. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Theodore Cohen, Thanapong Kreethadumrongdat, Xiaojun Liu & Vithalanand Kulkarni. (2001) Use of Aromatic Radical-Anions in the Absence of THF. Tandem Formation and Cyclization of Benzyllithiums Derived from the Attack of Homo- and Bishomoallyllithiums on α-Methylstyrenes:  Two-Pot Synthesis of Cuparene 1 . Journal of the American Chemical Society 123:15, pages 3478-3483.
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Dai Cheng, Shirong Zhu, Zhifang Yu & Theodore Cohen. (2000) The Magnesium−Ene Cyclization Stereochemically Directed by an Allylic Oxyanionic Group and Its Application to a Highly Stereoselective Synthesis of (±)-Matatabiether. Allylmagnesium Compounds by Reductive Magnesiation of Allyl Phenyl Sulfides 1 . Journal of the American Chemical Society 123:1, pages 30-34.
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Christopher J. Sinz & Scott D. Rychnovsky. 2001. Stereoselective Heterocyclic Synthesis III. Stereoselective Heterocyclic Synthesis III 51 92 .
Diego J. Ramón & Miguel Yus. (2000) New Methodologies Based on Arene-Catalyzed Lithiation Reactions and Their Application to Synthetic Organic Chemistry. European Journal of Organic Chemistry 2000:2, pages 225-237.
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Scott D. Rychnovsky, Alexandre J. Buckmelter, Vilas H. Dahanukar & Donald J. Skalitzky. (1999) Synthesis, Equilibration, and Coupling of 4-Lithio-1,3-dioxanes:  Synthons for syn - and a nti -1,3-Diols . The Journal of Organic Chemistry 64:18, pages 6849-6860.
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Claudio C Silveira, Gelson Perin, Antonio L Braga, Miguel J Dabdoub & Raquel G Jacob. (1999) Synthesis of ketene (S, Te)acetals and their transformation into Z-α-phenylthio-α,β-unsaturated aldehydes. Tetrahedron 55:24, pages 7421-7432.
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Fangping Chen, Boguslaw Mudryk & Theodore Cohen. (1999) Tandem reductive lithiations ? Carbanionic cyclizations yielding sulfur stabilized cyclopropyl- and cyclobutylcarbinyllithiums. Tetrahedron 55:11, pages 3291-3304.
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Izaskun Manteca, Bego?a Etxarri, Ainhoa Ardeo, Sonia Arrasate, I?aki Osante, Nuria Sotomayor & Esther Lete. (1998) Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones. Tetrahedron 54:40, pages 12361-12378.
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Alain Krief, Beno?t Kenda & Bruno Remacle. (1996) Stereoselective syntheses of 1,2-dialkyl-1-phenyl cyclopentanes involving intramolecular carbolithiation of ?-thioalkenes. Tetrahedron 52:21, pages 7435-7463.
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Alain Krief & Abdesslame Nazih. (1995) C/se bond cleavage of functionalized selenides by lithium arenides : Application to the geminal di-allylation of the carbonyl group of aldehydes and ketones.. Tetrahedron Letters 36:44, pages 8115-8118.
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Manfred Schlosser. 1994. Organometallics in Synthesis. Organometallics in Synthesis 1 166 .
Fangping Chen, Boguslaw Mudryk & Theodore Cohen. (1994) Generation, rearrangements and some synthetic uses of bishomoallyllithiums. Tetrahedron 50:45, pages 12793-12810.
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S. Achyutha Rao, Tso-Sheng Chou, Ioana Schipor & Paul Knochel. (1992) Preparation and Reactivity of Polyfunctional Zinc and Copper Organometallics Bearing Sulfur Functionalities. Tetrahedron 48:11, pages 2025-2043.
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Dennis W. McCullough, M. Bhupathy, Elvio Piccolino & Theodore Cohen. (1991) Highly efficient terpenoid pheromone syntheses via regio- and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers. Tetrahedron 47:47, pages 9727-9736.
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Miguel Yus & Diego J. Ramón. (1991) Arene-catalysed lithiation reactions with lithium at low temperature. J. Chem. Soc., Chem. Commun.:6, pages 398-400.
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Kazuhiko Tanaka, Keizaburo Minami, Ikuo Funaki & Hitomi Suzuki. (1990) Stereochemistry of sulfur-lithium and tin-lithium exchange reactions of functionalized cyclopropanes. Tetrahedron Letters 31:19, pages 2727-2730.
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Eric Block & Mohammad Aslam. (1988) The chemistry of mixed organosulfur-silicon compounds. Tetrahedron 44:2, pages 281-324.
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C.L. Bumgardner, J.R. Lever & S.T. Purrington. (1982) Preparation and synthetic utility of cyclopropyl phenyl sulfides. Tetrahedron Letters 23:23, pages 2379-2382.
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Theodore Cohen & James R. Matz. (1981) A synthesis of 2-vinylcylobutanones using 1-methoxycyclopropyllithium reagents. Tetrahedron Letters 22:26, pages 2455-2458.
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Isao Kuwajima & Ryo Takeda. (1981) Preparation of ?-trialkylsilyl ketones from ?-phenylseleno derivatives via their silyl enol ethers. Tetrahedron Letters 22:25, pages 2381-2384.
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Theodore Cohen, Daniel Ouellette, K. Pushpananda, A. Senaratne & Lin-Chen Yu. (1981) An economical and convenient preparation of 2-(phenylthio)cyclobutanone, a synthetic equivalent of cyclobutanone. Tetrahedron Letters 22:35, pages 3377-3380.
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David J. Ager. (1981) A new method for preparing 1-phenylthio-1-trimethylsilylalkanes: the preparation of ?-silylcarbanions and olefins.. Tetrahedron Letters 22:30, pages 2923-2926.
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T. COHEN & J. R. MATZ. (2016) ChemInform Abstract: REDUCTIVE LITHIATION OF SOME THIOKETALS USING LITHIUM 1‐(DIMETHYLAMINO)NAPHTHALENIDE. Chemischer Informationsdienst 11:33.
Crossref

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