View More View Less
  • 1 Norwegian University of Life Sciences, P.O. Box 5003, NO-1432 Ås, Norway
  • | 2 SINTEF Materials and Chemistry, P.O. Box 124 Blindern, NO-0314 Oslo, Norway
Restricted access

Conventional batch dibromocyclopropanations by reaction of bromoform and alkenes under phase-transfer conditions require strong base (50% NaOH (aq)), vigorous stirring, and often long reaction times. Using flow chemistry in a microreactor, the reactions were found to be smooth, rapid, and high-yielding under ambient conditions when 40% (w/w) NaOH was used as the base. The reaction has been tested with a representative selection of alkenes, displaying a variety of structural features.

  • 1.

    Skattebøl, L. Acta Chem. Scand. 1963, 17, 16831693.

  • 2.

    Kleveland, K.; Skattebøl, L. Acta Chem. Scand. 1975, B29, 191196.

  • 3.

    Skattebøl, L. Tetrahedron Lett. 1965, 6, 21752179.

  • 4.

    Holm, K. H.; Mohamed, E. A.; Skattebøl, L. Acta Chem. Scand. 1993, 47, 500505.

  • 5.

    Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1977, 18, 23472350.

  • 6.

    Arct, J.; Skattebøl, L.; Stenstrøm, Y. Acta Chem. Scand. 1983, B37, 681686.

  • 7.

    Skattebøl, L.; Stenstrøm, Y.; Stjerna, M.-B. Acta Chem. Scand. 1988, B42, 475483.

  • 8.

    Sydnes, L. K.; Holmelid, B.; Sengee, M.; Hanstein, M. J. Org. Chem. 2009, 74, 34303443.and references cited therein.

  • 9.

    Fedorynski, M. Chem. Rev. 2003, 103, 10991132. and references cited therein.

  • 10.

    Banwell, M. G.; Beck, D. A. S.; Stanislawski, P. C.; Sydnes, M. O.; Taylor, R.M. Curr. Org. Chem. 2005, 9, 15891600.

  • 11.

    Banwell, M. G.; Lehmann, A. L.; Menon, R. S.,Willis, A. C. Pure Appl. Chem. 2011, 83, 411423.

  • 12.

    Makosza, M.; Wawrzyniewicz, M. Tetrahedron Lett. 1969, 10, 46594662.

  • 13.

    Didriksen, T.; Skattebøl, L. Synth. Commun. 1999, 29, 10871095.

  • 14.

    Skattebøl, L.; Abskharoun, G. A.; Greibrokk, T. Tetrahedron Lett. 1973, 14, 13671370.

  • 15.

    Sirovski, F.; Gorokhova, M.; Ruban, S. J. Mol. Cat. A: Chemical 2003, 197, 213222.

  • 16.

    Starks, C. M. Tetrahedron 1999, 55, 62616274.

  • 17.

    Jas, G.; Kirschning, A. Chem. Eur. J. 2003, 9, 57085723.

  • 18.

    Geyer, K.; Codée, J. D. C.; Seeberger, P. H. Chem. Eur. J. 2006, 12, 84348442.

  • 19.

    Wiles, C.; Watts, P. Eur. J. Org. Chem. 2008, 2008, 16551671.

  • 20.

    Valera, F. E.; Quaranta, M.; Moran, A.; Blacker, J.; Armstrong, A.; Cabral, J. T.; Blackmond, D. G. Angew. Chem., Int. Ed. 2010, 49, 24782485.

    • Search Google Scholar
    • Export Citation
  • 21.

    Hartman, R. L.; McMullen, J. P.; Jensen, K. F. Angew. Chem., Int. Ed. 2011, 50, 75027519.

  • 22.

    Dummann, G.; Quittmann, U.; Gröschel, L.; Agar, D. W.; Wörz, O.; Morgenschweis, K. Catal. Today 2003, 79–80, 433439.

  • 23.

    Burns, J. R.; Ramshaw, C. Lab on a Chip 2001, 1, 1015.

  • 24.

    Kashid, M. N.; Gerlach, I.; Goetz, S.; Franzke, J.; Acker, J. F.; Platte, F.; Agar, D. W.; Turek, S. Ind. Eng. Chem. Res. 2005, 44, 50035010.

    • Search Google Scholar
    • Export Citation
  • 25.

    Ufer, A.; Mendorf, M.; Ghaini, A.; Agar, D. W. Chem. Eng. Technol. 2011, 34, 353360.

  • 26.

    Zhang, L.; Geng, M.; Teng, P.; Zhao, D.; Lu, X.; Li, J.-X. Ultrason. Sonochem. 2012, 19, 250256.

  • 27.

    Sinkovec, E.; Krajnc, M. Org. Process Res. Dev. 2011, 15, 817823.

  • 28.

    Xu, L. ; Brinker, U. H. In Synthetic Organic Sonochemistry; Luche, J.-L., Ed.; Springer Science+Business: New York, 1998; pp. 344345.

    • Search Google Scholar
    • Export Citation
  • 29.

    Ahmed-Omer, B.; Barrow, D.;Wirth, T. Chem. Eng. J. 2008, 135S, S280S283.

  • 30.

    Sipos, P. M.; Hefter, G.; May, P. M. J. Chem. Eng. Data 2000, 45, 613617.

  • 31.

    Jovanovic, J.; Rebrov, E. V.; Nijhuis, T. A. (Xander); Hessel, V.; Schouten, J. C. Ind. Eng. Chem. Res. 2010, 49, 26812687. and references cited therein.

    • Search Google Scholar
    • Export Citation
  • 32.

    Grupe, S.; Jacobi von Wangelin, A. ChemCatChem 2013, 5, 706710.

  • 33.

    Makosza, M.; Fedorynski, M. Synth. Commun. 1973, 3, 305309.

  • 34.

    Hackett, M.;Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 14491462.

  • 35.

    Dehmlow, E. V.; Franke, K. Liebigs Ann. Chem. 1979, 1979, 14561464.

  • 36.

    Abul Hashem, M. Ind. J. Chem., Sect. B 1988, 27B, 424429.

  • 37.

    Pettersen, A.; Jørgensen, E.; Sydnes, L. K. Acta Chem. Scand. 1990, 44, 603609.

  • 38.

    Skell, P. S.; Garner, A. Y. J. Am. Chem. Soc. 1956, 78, 54305433.

  • 39.

    Moss, R. A.; Joyce, M.A.;Huselton, J.K. Tetrahedron Lett. 1975, 16, 46214624.

  • 40.

    Sherrill, W. M.; Kim, R.; Rubin, M. Tetrahedron 2008, 64, 86108617.

  • 41.

    Doering, W. v. E.;Hoffmann, A. K. J. Am. Chem. Soc. 1954, 76, 61626165.

  • 42.

    Tsang, D. S.; Yang, S.; Alphonse, F.-A.; Yudin, A. K. Chem. Eur. J. 2008, 14, 886894.

  • 43.

    Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 17301740.

  • 44.

    Dale, W. J.; Swartzentruber, P. E. J. Org. Chem. 1959, 24, 955957.

  • 45.

    Binder, W. H.; Kurzhals, S.; Pulamagatta, B.; Decker, U.; Pawar, G. M.; Wang, D.; Kühnel, C.; Buchmeiser, M. R. Macromolecules 2008, 41, 84058412.

    • Search Google Scholar
    • Export Citation
  • 46.

    Seyferth, D.; Prokai, B. J. Org. Chem. 1966, 31, 17021704.

  • 47.

    Huang, N.-J.; Xu, L.-H. Chin. Sci. Bull. 1991, 36, 831834.

  • 48.

    Nefedov, O. M.; Novitskaya, N. N.; Petrov, A. D. Dokl. Akad. Nauk SSSR 1963, 152, 629632. (SciFinder Accession no: 1964:9387).

  • 49.

    Brun, P.; Casanova, J.; Hatem, J.; Vincent, E.-J.; Waegell, B.; Zahra, J.-P. C. R. Seances Acad. Sci., Ser. C 1979, 288, 201204.

  • 50.

    Taylor, K. G.; Hobbs, W. E.; Saquet, M. J. Org. Chem. 1971, 36, 369377.

  • 51.

    Huang, Y.-T.; Hsing, I.-T.; Tai, H.-I. Huaxue Xuebao 1964, 30, 306311. (SciFinder Accession no: 1964:476206).

  • 52.

    Vereshchagin, A. N.; Vul'fson, S. G.; Molostova, Z. A.; Arbuzov, B. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1971, 1971, 531537. (SciFinder Accession no: 1971: 463218).

    • Search Google Scholar
    • Export Citation
  • 53.

    Banwell, M. G.; Halton, B. Aust. J. Chem. 1979, 32, 26892699.

  • 54.

    Baird, M. S.;Baxter, A. G.W.;Devlin, B. R. J.; Searle, R. J.G. J. Chem. Soc., Chem. Commun. 1979, 8, 210211.

  • 55.

    Doering, W. v. E.; Henderson, Wm. A. Jr. J. Am. Chem. Soc. 1958, 80, 52745277.

  • 56.

    Hoeg, D. F.; Lusk, D. I.; Crumbliss, A. L. J. Am. Chem. Soc. 1965, 87, 41474155.

Manuscript Submission: HERE

  • Impact Factor (2019): 3.622
  • Scimago Journal Rank (2019): 0.795
  • SJR Hirsch-Index (2019): 20
  • SJR Quartile Score (2019): Q1 Chemistry (miscellenous)
  • SJR Quartile Score (2019): Q1 Fluid Flow and Transfer Processes
  • SJR Quartile Score (2019): Q2 Organic Chemistry
  • Impact Factor (2018): 2.277
  • Scimago Journal Rank (2018): 0.58
  • SJR Hirsch-Index (2018): 17
  • SJR Quartile Score (2018): Q1 Fluid Flow and Transfer Processes
  • SJR Quartile Score (2018): Q2 Organic Chemistry

Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation
2011
Volumes
per Year
1
Issues
per Year
4
Founder Áramlásos Kémiai Tudományos Társaság
Founder's
Address
H-1031 Budapest, Hungary Záhony utca 7.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)