Abstract:
Depending on the substituent at the triple bond, the reaction of 1-(alk-1-ynyl)-1-chlorocyclopropanes 1 with lithium monoalkylamides in THF gives hitherto unknown conjugated iminocyclopropenes 2 or 4-substituted 1,1-dimethylbuta-1,2-dienes 3 in up to 60% yields.
Document Type:
Article
Language: English
Citation:
K. N. Shavrin, V. D. Gvozdev, S. V. Yurov, O. M. Nefedov, “Unusual reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium monoalkylamides”, Mendeleev Commun., 18:1 (2008), 16–17
Linking options:
https://www.mathnet.ru/eng/mendc3231
https://www.mathnet.ru/eng/mendc/v18/i1/p16
This publication is cited in the following 10 articles:
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, “Alkynyl cyclopropanes in organic synthesis”, Russ Chem Bull, 73:1 (2024), 53
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
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes”, Mendeleev Commun., 31:5 (2021), 654–656
Shichao Yu, Shengming Ma, “How easy are the syntheses of allenes?”, Chem. Commun., 47:19 (2011), 5384
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Synthesis of 1-alkynyl-2-dialkylaminocyclopropanes and 1-alkynyl-2-diazolylcyclopropanes by reactions of 1-alkynyl-1-chlorocyclopropanes with amines and their lithium derivatives”, Russ Chem Bull, 59:2 (2010), 396
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Synthesis of 5-methylidenehexahydropyrrolo[l,2-a]imidazoles and 6-methylideneoctahydropyrrolo[l,2-a]pyrimidines by the reaction of 1-alkynyl-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes”, Russ Chem Bull, 59:7 (2010), 1451
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with arenethiols and alkanethiols in dimethyl sulfoxide in the presense of KOH”, Russ Chem Bull, 58:12 (2009), 2432
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Reaction of 1-(alk-1-ynyl)-1-halocyclopropanes with alcohols and phenol in KOH/DMSO as a method for the synthesis of 2-alkoxy-1-alkynyl- and 1-alkynyl-2-phenoxycyclopropanes”, Russ Chem Bull, 57:10 (2008), 2117
Konstantin N. Shavrin, Valentin D. Gvozdev, Serafim V. Yurov, Oleg M. Nefedov, “ChemInform Abstract: Unusual Reactions of 1‐(Alk‐1‐ynyl)‐1‐chlorocyclopropanes with Lithium Monoalkylamides.”, ChemInform, 39:28 (2008)
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “5-Methylenehexahydropyrrolo[1,2-a]imidazoles and 6-methyleneoctahydropyrrolo[1,2-a]pyrimidines in the reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes”, Mendeleev Commun., 18:6 (2008), 300–301
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