Abstract:
Alkaline hydrolysis of N-spiropentyl-N-nitrosourea at –50 °C generates unknown diazospiropentane in situ, which is trapped with methyl methacrylate or 3,3-dimethylcyclopropene yielding the corresponding 1-pyrazolines with a spiropentane fragment in the molecule. Some chemical transformations of the products obtained are performed.
Document Type:
Article
Language: English
Citation:
Yu. V. Tomilov, E. V. Shulishov, G. P. Okonnishnikova, O. M. Nefedov, “The first example of the generation and trapping of diazospiropentane by unsaturated compounds”, Mendeleev Commun., 7:5 (1997), 200–201
Linking options:
https://www.mathnet.ru/eng/mendc4855
https://www.mathnet.ru/eng/mendc/v7/i5/p200
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Roman A. Novikov, Denis D. Borisov, Maria A. Zotova, Dmitry A. Denisov, Yaroslav V. Tkachev, Victor A. Korolev, Evgeny V. Shulishov, Yury V. Tomilov, “Cascade Cleavage of Three-Membered Rings in the Reaction of D–A Cyclopropanes with 4,5-Diazaspiro[2.4]hept-4-enes: A Route to Highly Functionalized Pyrazolines”, J. Org. Chem., 83:15 (2018), 7836
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E. V. Shulishov, I. P. Klimenko, V. A. Korolev, I. V. Kostyuchenko, G. P. Okonnishnikova, Yu. V. Tomilov, “Azo-coupling and reduction of cyclopropanediazonium ions in the reactions with polyhydroxyarenes and aminophenols”, Russ Chem Bull, 57:8 (2008), 1703
I. P. Klimenko, Yu. V. Tomilov, “Pathways of decomposition of N-cyclopropyl N nitrosoureas in methanol”, Russ Chem Bull, 54:2 (2005), 366
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Yu. V. Tomilov, I. P. Klimenko, E. V. Shulishov, O. M. Nefedov, “Generation of diazo-2-methylenecyclopropane and its 1,3-dipolar cycloaddition to acrylates”, Russ Chem Bull, 49:7 (2000), 1207
Yu. V. Tomilov, I. V. Kostyuchenko, G. P. Okonnishnikova, E. V. Shulishov, E. A. Yagodkin, O. M. Nefedov, “Reactions of spirocyclopropane-containing 1- and 2-pyrazolines with electrophilic reagents”, Russ Chem Bull, 49:3 (2000), 472
Yu. V. Tomilov, I. V. Kostyuchenko, O. M. Nefedov, “Synthesis and properties of nitrogenous heterocycles containing a spiro-fused cyclopropane fragment”, Russian Chem. Reviews, 69:6 (2000), 461–480
YU. V. TOMILOV, E. V. SHULISHOV, G. P. OKONNISHNIKOVA, O. M. NEFEDOV, “ChemInform Abstract: The First Example of the Generation and Trapping of Diazospiropentane by Unsaturated Compounds.”, ChemInform, 29:10 (1998)
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