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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 8
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Original Articles

Facile Synthetic Method for the Preparation of Dithioacetals by the Double Conjugate Addition of Acetylenes Bearing Electron-Withdrawing Groups with Thiols

Hirofumi Kuroda Research Laboratory of Resources Utilization, Tokyo Institute of Technology, Nagatsuta-cho, 4259, Midori-ku, Yokohama, 226, JAPAN
,
Ikuyoshi Tomita Research Laboratory of Resources Utilization, Tokyo Institute of Technology, Nagatsuta-cho, 4259, Midori-ku, Yokohama, 226, JAPAN
&
Takeshi Endo Research Laboratory of Resources Utilization, Tokyo Institute of Technology, Nagatsuta-cho, 4259, Midori-ku, Yokohama, 226, JAPAN
Pages 1539-1543 | Received 11 Jul 1995, Published online: 15 Aug 2006

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Alexey V. Salin & Andrey A. Shabanov. (2023) Advances in organocatalysis of the Michael reaction by tertiary Phosphines. Catalysis Reviews 0:0, pages 1-90.
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Nobukazu Taniguchi & Kenji Kitayama. (2019) Zn-catalyzed dihydrosulfenylation of alkynes using thiols. Phosphorus, Sulfur, and Silicon and the Related Elements 194:7, pages 739-741.
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Gui-Sheng Deng, Zhi-Zhen Huang, Xiao-Chun Yu & Xian Huang. (2000) Direct Synthesis of α-Acyl Methylenetriphenylarsoranes from Readily Available Arsonium Salts. Synthetic Communications 30:14, pages 2487-2495.
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Articles from other publishers (34)

Tian-Jun Yue, Wei-Min Ren & Xiao-Bing Lu. (2023) Copolymerization Involving Sulfur-Containing Monomers. Chemical Reviews 123:24, pages 14038-14083.
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Dongseok Jang, Minchul Choi, Jinglong Chen & Chulbom Lee. (2022) Evolution of a Synthetic Strategy for Garsubellin A. Chemistry – A European Journal 28:71.
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Nobukazu Taniguchi & Kenji Kitayama. (2022) Metal Catalyzed-Introduction of Sulfur-Substituents to Unsaturated Carbon-Carbon Bonds金属触媒を用いた不飽和炭素-炭素結合への硫黄置換基の導入. Journal of Synthetic Organic Chemistry, Japan 80:4, pages 322-330.
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Vikas V. Khade, Archana S. Thube, Pankaj D. Dharpure & Ramakrishna G. Bhat. (2022) Direct synthesis of 1,3-dithiolanes from terminal alkynes via visible light photoredox catalysis . Organic & Biomolecular Chemistry 20:6, pages 1315-1319.
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Dongseok Jang, Minchul Choi, Jinglong Chen & Chulbom Lee. (2021) Enantioselective Total Synthesis of (+)‐Garsubellin A. Angewandte Chemie International Edition 60:42, pages 22735-22739.
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Dongseok Jang, Minchul Choi, Jinglong Chen & Chulbom Lee. (2021) Enantioselective Total Synthesis of (+)‐Garsubellin A. Angewandte Chemie 133:42, pages 22917-22921.
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Jin-Xia Lei, Qi-Yuan Wang, Fu-Sheng Du & Zi-Chen Li. (2021) Dynamic Ring-chain Equilibrium of Nucleophilic Thiol-yne “Click” Polyaddition for Recyclable Poly(dithioacetal)s. Chinese Journal of Polymer Science 39:9, pages 1146-1154.
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Joshua C. Worch, Connor J. StubbsMatthew J. PriceAndrew P. Dove. (2021) Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry. Chemical Reviews 121:12, pages 6744-6776.
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Tianyi Cheng, Wenming Huang, Di Gao, Zhe Yang, Congjie Zhang, Haixia Zhang, Jianjian Zhang, Hua Li & Xiao-Feng Yang. (2019) Michael Addition/S,N-Intramolecular Rearrangement Sequence Enables Selective Fluorescence Detection of Cysteine and Homocysteine. Analytical Chemistry 91:16, pages 10894-10900.
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Nobukazu Taniguchi & Kenji Kitayama. (2019) Dihydrosulfenylation of Alkynes with Thiols Using a Nickel Catalyst through a Radical Process. Asian Journal of Organic Chemistry 8:8, pages 1468-1471.
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Kenta Kishi, Shinobu Takizawa & Hiroaki Sasai. (2018) Phosphine-Catalyzed Dual Umpolung Domino Michael Reaction: Facile Synthesis of Hydroindole- and Hydrobenzofuran-2-Carboxylates. ACS Catalysis 8:6, pages 5228-5232.
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Alexey V. Salin, Anton V. Il'in, Rustem I. Faskhutdinov, Vladimir I. Galkin, Daut R. Islamov & Olga N. Kataeva. (2018) Tributylphosphine catalyzed addition of diphenylphosphine oxide to unsubstituted and substituted electron-deficient alkenes. Tetrahedron Letters 59:17, pages 1630-1634.
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Alberto Fraile, Alejandro Parra, Mariola Tortosa & José Alemán. (2014) Organocatalytic transformations of alkynals, alkynones, propriolates, and related electron-deficient alkynes. Tetrahedron 70:48, pages 9145-9173.
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Kohei Buniuchi & Takeshi Oriyama. (2012) Development of Catalyst-free Reactions Utilizing Characteristic Property of DMSO in the Presence of MS 4A. Journal of Synthetic Organic Chemistry, Japan 70:10, pages 1041-1053.
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Tomoko Kakinuma & Takeshi Oriyama. (2010) Double Michael addition of dithiols to acetylenic carbonyl compounds under the influence of molecular sieve and dimethyl sulfoxide. Tetrahedron Letters 51:2, pages 290-292.
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Sumit Mukherjee, Dimitra Kontokosta, Aditi Patil, Sivakumar Rallapalli & Daesung Lee. (2009) Improved Method for the Synthesis of β-Carbonyl Silyl-1,3-Dithianes by the Double Conjugate Addition of 1,3-Dithiol to Propargylic Carbonyl Compounds. The Journal of Organic Chemistry 74:23, pages 9206-9209.
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Sumit Mukherjee & Daesung Lee. (2009) Application of Tandem Ring-Closing Enyne Metathesis: Formal Total Synthesis of (−)-Cochleamycin A. Organic Letters 11:13, pages 2916-2919.
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Helen E. Randell-Sly, James D. Osborne, Robert L. Woodward, Gordon S. Currie & Michael C. Willis. (2009) Intermolecular rhodium catalyzed hydroacylation of allenes: the regioselective synthesis of β,γ-unsaturated ketones. Tetrahedron 65:26, pages 5110-5117.
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Hoi‐Yan Shiu, Tak‐Chung Chan, Chi‐Ming Ho, Yungen Liu, Man‐Kin Wong & Chi‐Ming Che. (2009) Electron‐Deficient Alkynes as Cleavable Reagents for the Modification of Cysteine‐Containing Peptides in Aqueous Medium. Chemistry – A European Journal 15:15, pages 3839-3850.
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Scott E. Denmark & Gregory L. Beutner. (2008) Lewis Base Catalysis in Organic Synthesis. Angewandte Chemie International Edition 47:9, pages 1560-1638.
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Scott E. Denmark & Gregory L. Beutner. (2008) Lewis‐Base‐Katalyse in der organischen Synthese. Angewandte Chemie 120:9, pages 1584-1663.
Crossref
Brindaban C. Ranu & Tanmay Mandal. (2007) A Simple, Efficient, and Green Procedure for the 1,4-Addition of Thiols to Conjugated Alkenes and Alkynes Catalyzed by Sodium Acetate in Aqueous Medium. Australian Journal of Chemistry 60:3, pages 223.
Crossref
Brindaban C. Ranu, Subhash Banerjee & Ranjan Jana. (2007) Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds. Tetrahedron 63:3, pages 776-782.
Crossref
Michael C. Willis, Helen E. Randell-Sly, Robert L. Woodward, Steven J. McNally & Gordon S. Currie. (2006) Rhodium-Catalyzed Intermolecular Chelation Controlled Alkene and Alkyne Hydroacylation:  Synthetic Scope of β- S -Substituted Aldehyde Substrates . The Journal of Organic Chemistry 71:14, pages 5291-5297.
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Helen F. SneddonAlexandra van den HeuvelAnna K. H. HirschRichard A. BoothDavid M. ShawMatthew J. GauntSteven V. Ley. (2006) Double Conjugate Addition of Dithiols to Propargylic Carbonyl Systems To Generate Protected 1,3-Dicarbonyl Compounds. The Journal of Organic Chemistry 71:7, pages 2715-2725.
Crossref
Michael C. Willis, Helen E. Randell-Sly, Robert L. Woodward & Gordon S. Currie. (2005) Chelation-Controlled Intermolecular Alkene and Alkyne Hydroacylation: The Utility of β-Thioacetal Aldehydes. Organic Letters 7:11, pages 2249-2251.
Crossref
V. Reboul, J.-F. Brière & P. Metzner. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 271 322 .
I.J.S. Fairlamb & J.M. Dickinson. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 1177 1259 .
Joey L. Methot & William R. Roush. (2004) Nucleophilic Phosphine Organocatalysis. Advanced Synthesis & Catalysis 346:9-10, pages 1035-1050.
Crossref
Matthew J. Gaunt, Helen F. Sneddon, Peter R. Hewitt, Paolo Orsini, David F. Hook & Steven V. Ley.. (2003) Development of β-keto 1,3-dithianes as versatile intermediates for organic synthesis. Org. Biomol. Chem. 1:1, pages 15-16.
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Xiyan Lu, Chunming Zhang & Zhenrong Xu. (2001) Reactions of Electron-Deficient Alkynes and Allenes under Phosphine Catalysis. Accounts of Chemical Research 34:7, pages 535-544.
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Xavier Ariza, Anna M. Costa, Montserrat Faja, Oriol Pineda & Jaume Vilarrasa. (2000) New Protecting Groups for 1,2-Diols (Boc- and Moc-ethylidene). Cleavage of Acetals with Bases. Organic Letters 2:18, pages 2809-2811.
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Geoffrey T. Crisp & Michael J. Millan. (1998) Conjugate addition of amino acid side chains to alkynones and alkynoic acid derivatives. Tetrahedron 54:3-4, pages 637-648.
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H. KURODA, I. TOMITA & T. ENDO. (2010) ChemInform Abstract: Facile Synthetic Method for the Preparation of Dithioacetals by the Double Conjugate Addition of Acetylenes Bearing Electron‐Withdrawing Groups with Thiols.. ChemInform 27:32.
Crossref

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