Abstract
Gas-phase pyrolysis of of 1-chloro-1-fluoro-2-methylcyclopropanes in an empty or filled with quartz pieces flow-tube reactor at 430—460 °C gives 2-fluorobuta-1,3-dienes (in 42—75% yields), whereas pyrolysis in the presence of Al2O3 at 150—250 °C gives 2-chlorobuta-1,3-dienes as the major products (in 58—68% yield).
Similar content being viewed by others
References
(a) H. Jendralla, Cyclopropyl to Allyl Rearrengement, in Methods of Organic Chemistry (Houben-Weyl), Vol. E17c, Ed. A. de Meijere, Thieme, Stuttgart, 1997, 2313; (b) R. R. Kos-tikov, A. P. Molchanov, H. Hopf, Top. Curr. Chem., 1990, 155, 41; (c) M. Fedorynski, Chem. Rev., 2003, 103, 1099; (d) W. R. Dolbier, Jr., M. A. Battiste, Chem. Rev., 2003, 103, 1071; (e) R. Bartlet, Y. Quang, Bull. Soc. Chim. Fr., 1969, 3729; (f) M. Schlosser, Tetrahedron, 1978, 34, 3.
(a) R. Fields, R. N. Haszeldine, D. Peter, J. Chem. Soc. (C), 1969, 165—172; (b) K. A. Holbrook, K. A. W. Parry, J. Chem. Soc. (B), 1970, 1019.
(a) N. V. Volchkov, M. A. Novikov, M. B. Lipkind, O. M. Nefedov, Mendeleev Commun., 2013, 19—23; (b) M. A. No-vikov, N. V. Volchkov, M. B. Lipkind, O. M. Nefedov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 71 [Izv. Akad. Nauk, Ser. Khim., 2013, 71].
(a) G. C. Robinson, J. Org. Chem., 1968, 33, 607—610; (b) M. S. Baird, B. S. Mahli, L. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1990, 1881—1886; (c) R. P. Clifford, K. A. Holbrook, J. Chem. Soc., Perkin Trans. 2, 1972, 1972–1974.
N. V. Volchkov, M. B. Lipkind, A. V. Zabolotskikh, A. V. Ignatenko, O. M. Nefedov, Mendeleev Commun., 2006, 153.
(a) P. Weyerstahl, D. Klamann, C. Finger, M. Fligge, F. Nerdel, J. Buddrus, Chem. Ber., 1968, 101, 1303—1311; (b) C. Finger, F. Nerdel, P. Weyerstahl, J. Buddrus, D. Kla-mann, Deutsches Patentant 1235293 (1967); Chem. Abstr., 1967, 66, 115286.
E. V. Guseva, N. V. Volchkov, Yu. V. Tomilov, O. M. Nefe-dov, Eur. J. Org. Chem., 2004, 14, 3136–3144.
T. B. Patrick, J. Rogers, K. Gorrell, Org. Lett., 2002, 4, 3155.
O. M. Nefedov, N. V. Volchkov, Mendeleev Commun., 2006, 121–128.
(a) O. M. Nefedov, A. A. Ivashenko, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1968, 17, 445 [Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 446]; (b) O. M. Nefedov, A. A. Ivashenko, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1968, 17, 1346 [Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 1417]; (c) N. V. Volchkov, A. V. Zabolotskikh, A. V. Ignatenko, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1990, 39, 1458 [Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1609]; (d) N. V. Volchkov, A. V. Zabolotskikh, M. B. Lipkind, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 1782 [Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1935].
W. E. Parham, R. R. Twelves, J. Org. Chem., 1957, 22, 730.
M. Christl, M. Braun, H. Fischer, S. Groetsch, G. Muller, D. Leusser, S. Deuerlein, D. Stalke, M. Arnone, B. Engels, Eur. J. Org. Chem., 2006, 5045.
W. R.Jr. Dolbier, J. J. Keaffaber, C. R. Burkholder, H. Ko-roniac, J. Pradhan, Tetrahedron, 1992, 48, 9649.
C. W. Jefford, A. N. Kabengele, U. Burger, Tetrahedron Lett., 1972, 4799.
L. Chosez, G. Slinckx, M. Glineur, R. Hoet, P. Laroche, Tetrahedron Lett., 1967, 2773.
N. V. Volchkov, A. V. Zabolotskikh, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1990, 39, 211 [Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 228].
H. J. Relch, I. L. Relch, K. E. Yelm, J. E. Holladay, D. Gschneidner, J. Am. Chem. Soc., 1993, 115, 6625.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2250–2254, October, 2014.
Rights and permissions
About this article
Cite this article
Volchkov, N.V., Lipkind, M.B., Novikov, M.A. et al. Gas-phase pyrolysis of 1-chloro-1-fluoro-2-methylcyclopropanes in the presence of SiO2 or Al2O3 with the formation of 2-chloro- or 2-fluorobuta-1,3-dienes. Russ Chem Bull 63, 2250–2254 (2014). https://doi.org/10.1007/s11172-014-0730-4
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-014-0730-4