Abstract:
Bis(2-phenylethyl)phosphine oxide and sulfide react with 3-phenyl-2-propynenitrile in the presence of KOH under mild conditions to form unexpectedly α,β-diadducts, 2,3-bis[bis(2-phenylethyl)phosphoryl]- and 2,3-bis[bis(2-phenylethyl)phosphorothioyl]-3-phenylpropionitriles.
Document Type:
Article
Language: English
Citation:
S. N. Arbuzova, N. K. Gusarova, M. V. Bogdanova, N. I. Ivanova, I. A. Ushakov, A. G. Mal'kina, B. A. Trofimov, “Unexpected double α,β-addition of secondary phosphine chalcogenides to 3-phenyl-2-propynenitrile”, Mendeleev Commun., 15:5 (2005), 183–184
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This publication is cited in the following 13 articles:
P. A. Volkov, S. I. Verkhoturova, S. N. Arbuzova, K. O. Khrapova, I. A. Bidusenko, S. V. Zinchenko, B. A. Trofimov, Mendeleev Commun., 35:2 (2025), 158–161
P. A. Volkov, N. K. Gusarova, K. O. Khrapova, A. A. Telezhkin, A. I. Albanov, S. F. Vasilevskii, B. A. Trofimov, “A mechanistic insight into the chemoselectivity of the reaction between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids”, Mendeleev Commun., 31:5 (2021), 670–672
Divya Bhatt, Chandresh Kumari, Avijit Goswami, “Syntheses and Applications of 2‐Alkynylnitriles”, Asian J Org Chem, 8:11 (2019), 1985
Kolio D. Troev, Reactivity of P-H Group of Phosphorus Based Compounds, 2018, 145
Frank Strehler, Marcus Korb, Tobias Rüffer, Alexander Hildebrandt, Heinrich Lang, “Synthesis and isomerization behavior of cyano-vinyl ferrocenes”, Journal of Organometallic Chemistry, 820 (2016), 89
Alexander V. Artem'ev, Nataliya A. Chernysheva, Svetlana V. Yas'ko, Nina K. Gusarova, Irina Yu Bagryanskaya, Boris A. Trofimov, “Straightforward Solvent‐Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron‐Rich Alkenes, and Elemental Sulfur or Selenium”, Heteroatom Chemistry, 27:1 (2016), 48
S. F. Malysheva, N. A. Belogorlova, V. A. Kuimov, N. I. Ivanova, P. A. Volkov, I. A. Ushakov, N. K. Gusarova, B. A. Trofimov, “Atom-sparing synthesis of tertiary diphosphine dichalcogenides from acetylenes and secondary phosphine chalcogenides”, Russ J Gen Chem, 80:2 (2010), 232
N. K. Gusarova, S. F. Malysheva, N. A. Belogorlova, V. A. Kuimov, I. A. Ushakov, B. A. Trofimov, “Nucleophilic diaddition of secondary phosphine sulfides to acetylene and methylacetylene”, Russ Chem Bull, 58:1 (2009), 234
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
Tatyana E. Glotova, Marina Yu. Dvorko, Nina K. Gusarova, Svetlana N. Arbuzova, Igor A. Ushakov, Tatyana I. Kazantseva, Boris A. Trofimov, “Chemo- and Regiospecific Monoaddition of Secondary Phosphine Sulfides to 1-Acyl-2-phenylacetylenes”, Phosphorus, Sulfur, and Silicon and the Related Elements, 183:6 (2008), 1396
N. K. Gusarova, N. I. Ivanova, S. F. Malysheva, A. V. Artem'ev, B. V. Timokhin, B. A. Trofimov, “First example of alkylation of secondary phosphine selenides”, Russ J Gen Chem, 78:8 (2008), 1628
G. Keglevich, Organophosphorus Chemistry, 2007, 73
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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