Abstract
The reaction of 1,1-dihydropolyfluoroalkyl benzyl sulfones with sodium azide or trimethylsilyl azide in the presence of tertiary amines gives ammonium salts of 4-benzylsulfonyl-5-polyfluoroalkyl-ν-triazoles. The proposed reaction scheme includes the participation of catalytic amounts of azide ion in the cyclization of the formed intermediate vinyl azides to triazoles. X-ray analysis of 1,4-diazabicyclo[2.2.2]octane salt of 4-benzylsulfonyl-5-(ω-H-hexafluoropropyl)-ν-triazole has been carried out.
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REFERENCES
V. M. Timoshenko, V. V. Listvan, E. B. Rusanov, Yu. G. Shermolovich, and L. N. Markovskii, Zh. Org. Khim., 33, 70 (1997).
Yu. G. Shermolovich, V. M. Timoshenko, V. V. Listvan and L. N. Markovskii. Zh. Org. Khim., 34, 1167 (1998).
V. M. Timoshenko, Ya. V. Nikolin, N. P. Kolesnik, and Yu. G. Shermolovich, Zh. Org. Khim.(in press).
I. H. Boyer and F. C. Canter, Chem. Rev., 54, 1 (1954).
N. S. Zefirov and N. K. Chapovskaya, Zh. Org. Khim., 6, 2596 (1970).
N. S. Zefirov, N. K. Chapovskaya, and V. V. Kolesnikov, Chem. Commun., No. 17, 1001 (1971).
A. N. Nesmeyanov and M. N. Rybinskaya, Dokl. Akad. Nauk, 167, 109 (1966).
S. Maoirana, D. Pocar, and P. Dalla Croce, Tetrahedron Lett., No 48, 6043 (1966).
N. P. Stepanova, V. A. Galishev, E. S. Turbanova, A. V. Maleev, K. A. Potekhin, E. N. Kurkutova, Yu. T. Struchkov, and A. A. Petrov, Zh. Org. Khim., 25, 1612 (1989).
G. G. Bargamov, K. A. Lysenko, M. D. Bargamov, and Yu. T. Struchkov, Izv. Akad. Nauk, Ser. Khim., 2465 (1995).
V. A. Naumov and O. N. Kataeva, Molecular Structure of Organic Compounds of Oxygen and Sulfur in the Gaseous Phase[in Russian], Nauka, Minsk (1990), p. 192.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1 (1987).
L. N. Kuleshova and P. M. Zorkii, Acta Crystallogr. (B), 37, 1363 (1981).
I. E. Kalinichenko, Zh. Obshch. Khim., 54, 998 (1984).
D. J. Watkin, C. K. Prout, J. R. Carruthers, and P. W. Betteridge, CRYSTALS, Issue 10, Chemical Crystallography Laboratory, Oxford University (1966).
A. C. T. North, D. C. Phillips, F. Scott, and F. S. Matthews, Acta Crystallogr. (A), 24, 351 (1968).
J. R. Carruthers and D. J. Watkin, Acta Crystallogr. (A), 35, 698 (1979).
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Timoshenko, V.M., Nikolin, Y.V., Chernega, A.N. et al. Synthesis of 4-Benzylsulfonyl-5-polyfluoroalkyl-ν-triazoles from 1,1-Dihydropolyfluoroalkyl Benzyl Sulfones. Chemistry of Heterocyclic Compounds 37, 470–476 (2001). https://doi.org/10.1023/A:1017604021697
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DOI: https://doi.org/10.1023/A:1017604021697