Abstract:
The (alk-1-ynyl)halocarbenes 4 have been generated from 3-substituted 1,1,1,3-tetrahalopropanes 1 via elimination of three molecules of hydrogen halide by treatment with ButOK or with alkali metal hydroxides under phase-transfer catalysis conditions and have been trapped by alkenes to form 1-(alk-1-ynyl)-1-halocyclopropanes 5 in 40–70% yields.
Document Type:
Article
Language: English
Citation:
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “A new general method for the generation of (alk-1-ynyl)halocarbenes by base solvolysis of 3-substituted 1,1,1,3-tetrahalopropanes”, Mendeleev Commun., 7:4 (1997), 144–145
Linking options:
https://www.mathnet.ru/eng/mendc4826
https://www.mathnet.ru/eng/mendc/v7/i4/p144
This publication is cited in the following 8 articles:
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Methods for the synthesis of functionalized alkynylcyclopropanes”, Russ Chem Bull, 70:11 (2021), 2051
Bastian Bernhardt, Marcel Ruth, André K. Eckhardt, Peter R. Schreiner, “Ethynylhydroxycarbene (H–C≡C–C̈–OH)”, J. Am. Chem. Soc., 143:10 (2021), 3741
Yu. V. Tomilov, L. G. Menchikov, E. A. Shapiro, V. D. Gvozdev, K. N. Shavrin, N. V. Volchkov, M. B. Lipkind, M. P. Egorov, S. E. Boganov, V. N. Khabashesku, E. G. Baskir, “Carbenes, related intermediates, and small-sized cycles: contribution from Professor Nefedov's laboratory”, Mendeleev Commun., 31:6 (2021), 750–768
Esfir G. Baskir, Valentin D. Gvozdev, Konstantin N. Shavrin, Mikhail P. Egorov, Oleg M. Nefedov, “Infrared-Spectroscopic Study of (4-Methylpent-3-en-1-ynyl)methylthiocarbene, Its Photochemical Transformations, and Reactions in an Argon Matrix”, J. Phys. Chem. A, 123:42 (2019), 9175
Sergey E. Boganov, Valery I. Faustov, Konstantin N. Shavrin, Valentin D. Gvozdev, Vladimir M. Promyslov, Mikhail P. Egorov, Oleg M. Nefedov, “A Highly Delocalized Triplet Carbene, 5-Methylhexa-1,2,4-triene-1,3-diyl: Matrix IR Identification, Structure, and Reactions”, J. Am. Chem. Soc., 131:41 (2009), 14688
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Synthesis of (alk-1-ynyl)cyclopropenium salts via the reaction of (alk-1-ynyl)chlorocarbenes with diphenylacetylene”, Mendeleev Commun., 9:3 (1999), 99–101
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Alkynylhalocarbenes”, Russ Chem Bull, 47:6 (1998), 1154
K. N. SHAVRIN, V. D. GVOZDEV, O. M. NEFEDOV, “ChemInform Abstract: A New General Method for the Generation of (Alk‐1‐ynyl)halocarbenes by Base Solvolysis of 3‐Substituted 1,1,1,3‐Tetrahalopropanes.”, ChemInform, 28:49 (1997)
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