M. E. Shemakhina, A. V. Nemtarev, D. V. Chachkov, S. A. Pukhov, V. F. Mironov, “Phosphonium and arsonium salts based on alantolactone”, Mendeleev Commun., 33:6 (2023), 759

Communications

Phosphonium and arsonium salts based on alantolactone

M. E. Shemakhina^a, A. V. Nemtarev^b, D. V. Chachkov^c, S. A. Pukhov^d, V. F. Mironov^b

^a Alexander Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russian Federation
^b A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^c Kazan Department of Joint Supercomputer Center, Scientific Research Institute for System Analysis, Russian Academy of Sciences, Kazan, Russian Federation
^d Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

Аннотация: The reaction of alantolactone, a sesquiterpene α,β-unsaturated lactone, with H-phosphonium or H-arsonium triflates proceeds as P–H or As–H addition at the terminal =CH₂ moiety to afford novel triphenyl(sesquiterpenyl)phosponium or -arsonium triflates. Their diastereoisomerism at the formed C¹¹ chiral center has been simulated by quantum chemical calculations.

Ключевые слова: sesquiterpenes, lactone, alantolactone, addition reaction, phosphonium salts, arsonium salts, quantum chemical calculations.

Язык публикации: английский

DOI: 10.1016/j.mencom.2023.10.006

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