Abstract:
Secondary phosphine sulfides react stereo- and regioselectively with aryl and hetaryl acetylenes in the presence of radical initiators (AIBN, 60–65 °C) in the anti-Markovnikov mode giving Z-isomers of the corresponding monoadducts in high yields.
Document Type:
Article
Language: English
Citation:
B. A. Trofimov, S. F. Malysheva, N. K. Gusarova, N. A. Belogorlova, S. F. Vasilevskii, V. B. Kobychev, B. G. Sukhov, I. A. Ushakov, “Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity”, Mendeleev Commun., 17:3 (2007), 181–182
Linking options:
https://www.mathnet.ru/eng/mendc3419
https://www.mathnet.ru/eng/mendc/v17/i3/p181
This publication is cited in the following 15 articles:
S. F. Vasilevsky, A. A. Stepanov, “Alkyl, Aryl, and Hetaryl Acetylenes: Highly Reactive Multifunctional Compounds (A Review)”, Russ J Gen Chem, 93:10 (2023), 2417
S. F Vasilevsky, A. A Stepanov, “Alkyl, aryl and hetaryl acetylenes - highly reactive multifunctional compounds (a review)”, Žurnal obŝej himii, 93:10 (2023), 1479
Pavel A. Volkov, Nina K. Gusarova, Kseniya O. Khrapova, Anton A. Telezhkin, Nina I. Ivanova, Alexander I. Albanov, Boris A. Trofimov, “Catalyst-free selenylation of acylacetylenes with secondary phosphine selenides and water: A short-cut to bis(2-acylvinyl) selenides”, Journal of Organometallic Chemistry, 867 (2018), 79
Yanina Moglie, María José González-Soria, Iris Martín-García, Gabriel Radivoy, Francisco Alonso, “Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes”, Green Chem., 18:18 (2016), 4896
O. M. Demchuk, M. Stankevič, K. M. Pietrusiewicz, Knowledge Updates 2015/1, 2015
P. A. Volkov, N. I. Ivanova, K. O. Khrapova, A. I. Albanov, S. N. Arbuzova, N. K. Gusarova, B. A. Trofimov, “Synthesis of new N-phosphorylated vinylhydropyridines”, Russ J Gen Chem, 85:8 (2015), 1978
Xiang-Qiang Pan, Jian-Ping Zou, Wen-Bin Yi, Wei Zhang, “Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds”, Tetrahedron, 71:40 (2015), 7481
Zili Chen, Yu‐Xin Zhang, Yan An, Xin‐Li Song, Ya‐Hui Wang, Li‐Li Zhu, Lin Guo, “Radical Addition of Ethers to Terminal Alkynes with High E‐Selectivity”, Eur J Org Chem, 2009:30 (2009), 5146
Boris A. Trofimov, Nina K. Gusarova, Svetlana N. Arbuzova, Nina I. Ivanova, Alexander V. Artem'ev, Pavel A. Volkov, Igor' A. Ushakov, Svetlana F. Malysheva, Vladimir A. Kuimov, “Stereoselective free-radical addition of secondary phosphine selenides to aromatic acetylenes”, Journal of Organometallic Chemistry, 694:5 (2009), 677
B. A. Trofimov, N. K. Gusarova, “Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free 'green' organophosphorus chemistry”, Mendeleev Commun., 19:6 (2009), 295–302
Massimo Di Vaira, Maurizio Peruzzini, Stefano Seniori Costantini, Piero Stoppioni, “Reactivity of thiophosphinous acid bound to ruthenium”, Journal of Organometallic Chemistry, 693:18 (2008), 3011
Boris A. Trofimov, Svetlana F. Malysheva, Nina K. Gusarova, Nataliya A. Belogorlova, Sergei F. Vasilevsky, Vladimir B. Kobychev, Boris G. Sukhov, Igor A. Ushakov, “Free‐Radical Addition of Phosphine Sulfides to Aryl and Hetaryl Acetylenes: Unpresedented Stereoselectivity.”, ChemInform, 38:42 (2007)
S. N. Arbuzova, N. K. Gusarova, M. V. Bogdanova, I. A. Ushakov, A. G. Mal'kina, B. A. Trofimov, “Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts”, Mendeleev Commun., 17:6 (2007), 325–326
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