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Mendeleev Communications, 1992, Volume 2, Issue 1, Pages 13–15
DOI: https://doi.org/10.1070/MC1992v002n01ABEH000099
(Mi mendc5370)
 

This article is cited in 28 scientific papers (total in 28 papers)

Cyclopropanation of Unsaturated Compounds with Diazomethane Generated in situ: A New Efficient and Practical Route to Cyclopropane Derivatives

O. M. Nefedova, Yu. V. Tomilova, A. B. Kostitsyna, U. M. Dzhemilevb, V. A. Dokitchevc

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
c Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
Abstract: The synthesis of the title compounds is easily achieved by the Pd-catalysed cyclopropanation of unsaturated compounds with diazomethane generated in situ from N-methyl-N-nitrosourea–KOH in CH2Cl2–Et2O.
Document Type: Article
Language: English


Citation: O. M. Nefedov, Yu. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokitchev, “Cyclopropanation of Unsaturated Compounds with Diazomethane Generated in situ: A New Efficient and Practical Route to Cyclopropane Derivatives”, Mendeleev Commun., 2:1 (1992), 13–15
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  • https://www.mathnet.ru/eng/mendc/v2/i1/p13
  • This publication is cited in the following 28 articles:
    1. Arslan R. Akhmetov, Arthur R. Tulyabaev, Denis Sh. Sabirov, “C 60 –bicyclo[2.2.1]heptanes: new hybrid mono- and hexakis-adducts of the C 60 fullerene”, Fullerenes, Nanotubes and Carbon Nanostructures, 33:1 (2025), 12  crossref
    2. Yuan Yao, Xinyue Zhang, Yingying Cao, Long Liu, Yanqiang Zhang, Suojiang Zhang, “Single-Site Pd Regulated by π-π Stacking for High-Selectivity Cyclopropanation Reaction”, J. Am. Chem. Soc., 146:45 (2024), 31053  crossref
    3. Yury V. Tomilov, Anatoly I. Kazakov, Aleksander A. Molokanov, Olga A. Pantyukh, Evgeny V. Shulishov, Leonid G. Menchikov, Albina V. Nabatova, Tatyana S. Larikova, Natalya I. Varlamova, Leonid S. Yanovsky, “Thermochemical and physical characteristics of isomeric tetracycloundecanes obtained from endo- and exo-dicyclopentadienes”, Fuel, 373 (2024), 132294  crossref
    4. Wei Wang, Baian Pu, Chi Ma, Chengxiang Shi, Lun Pan, Xiangwen Zhang, Ji‐Jun Zou, “Pd/C catalytic cyclopropanation of polycyclic olefins for synthesis of high‐energy‐density strained fuels”, AIChE Journal, 69:7 (2023)  crossref
    5. E. V. Shulishov, O. A. Pantyukh, L. G. Menchikov, Yu. V. Tomilov, “Catalytic cyclopropanation of hexa-1,3,5-triene with diazomethane as a simple synthesis of high-energy tercyclopropane”, Mendeleev Commun., 33:4 (2023), 512–514  mathnet  crossref
    6. Jillian W. Sheeran, Kiersten Campbell, Christopher P. Breen, Gerald Hummel, Changfeng Huang, Anamika Datta, Serge H. Boyer, Scott J. Hecker, Matthew M. Bio, Yuan-Qing Fang, David D. Ford, M. Grace Russell, “Scalable On-Demand Production of Purified Diazomethane Suitable for Sensitive Catalytic Reactions”, Org. Process Res. Dev., 25:3 (2021), 522  crossref
    7. 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  mathnet  crossref
    8. L. G. Menchikov, E. V. Shulishov, Yu. V. Tomilov, “Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane”, Russian Chem. Reviews, 90:2 (2021), 199–230  mathnet  mathnet  crossref  isi  scopus
    9. E. V. Shulishov, O. A. Pantyukh, L. G. Menchikov, Yu. V. Tomilov, “Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane”, Mendeleev Commun., 30:5 (2020), 612–614  mathnet  crossref
    10. Evgeny V. Shulishov, Olga A. Pantyukh, Leonid G. Menchikov, Yury V. Tomilov, “Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane”, Tetrahedron Letters, 60:31 (2019), 2043  crossref
    11. Samuel Jordi, Philip Kraft, “Crossing the Boundaries between Marine and Muguet: Discovery of Unusual Lily‐of‐the‐Valley Odorants Devoid of Aldehyde Functions”, Helvetica Chimica Acta, 101:6 (2018)  crossref
    12. Yu. V. Tomilov, L. G. Menchikov, R. A. Novikov, O. A. Ivanova, I. V. Trushkov, “Methods for the synthesis of donor-acceptor cyclopropanes”, Russian Chem. Reviews, 87:3 (2018), 201–250  mathnet  mathnet  crossref  isi  scopus
    13. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Fieser and Fieser's Reagents for Organic Synthesis, 2017  crossref
    14. Doris Dallinger, Vagner D. Pinho, Bernhard Gutmann, C. Oliver Kappe, “Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane”, J. Org. Chem., 81:14 (2016), 5814  crossref
    15. T. R. Belderrain, M. C. Nicasio, C-1 Building Blocks in Organic Synthesis 1, 2014  crossref
    16. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Fieser and Fieser's Reagents for Organic Synthesis, 2013, 203  crossref
    17. Bill Morandi, Erick M. Carreira, “Iron-Catalyzed Cyclopropanation in 6 M KOH with in Situ Generation of Diazomethane”, Science, 335:6075 (2012), 1471  crossref
    18. Michael A. Emerzian, William Davenport, Jiangao Song, Jim Li, Ihsan Erden, “Palladium‐Catalyzed Cyclopropanation of Unsaturated Endoperoxides. A New Peroxide‐Preserving Reaction”, Adv Synth Catal, 351:7-8 (2009), 999  crossref
    19. A. R. Tuktarov, V. V. Korolev, L. M. Khalilov, A. G. Ibragimov, Yu. M. Dzhemilev, “Catalytic cyclopropanation of fullerene[60] with diazomethane”, Russ J Org Chem, 45:11 (2009), 1594  crossref
    20. Ilfir R. Ramazanov, Leisan K. Dil'mukhametova, Leonard M. Khalilov, Usein M. Dzhemilev, Oleg M. Nefedov, “Diastereoselective conversion of alkynyl(trimethyl)silanes into substituted cyclopropanes affected by the i-Bu3Al–CH2I2 reagent”, Tetrahedron Letters, 49:42 (2008), 6058  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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