Studies on tellurium-containing heterocycles. Part 10.¹ 2-Benzotelluropyrylium salts: first preparation and reactions with Grignard reagents

Abstract

The first simple preparation of 2-benzotelluropyrylium salts 4 from o-ethynylbenzyl bromides 1 in two steps, and the characteristic reaction of these salts 4 with benzylmagnesium bromide and other Grignard reagents are described.

References

1. For part 9, see H. Sashida, Heterocycles, 1998, 48, 631.
2. (a)A. T. Balaban, A. Dinculescu, G. N. Dorofeenko, G. W. Fischer, A. V. Koblik, V. V. Mezhritskii and W. Schroth, Advances in Heterocyclic Chemistry: Pyrulium Salts: Synthesis, Reactions, and Physical Properties, Supplement 2, ed. A. R. Katrizky, Academic Press, Inc., London, 1982.
3. G. Doddi and G. Ercolani, Advances in Heterocyclic Chemistry: Thiopyrylium, Selenopyrylium, and Telluropyrylium Salts, vol. 60, ed. A. R. Katritzky, Academic Press, Inc., London, 1994, pp. 65–195.
4. (a) M. Renson and P. Pirson, Bull. Soc. Chim. Belg., 1966, 75, 456; (b) A. Tadino, L. Christiaens and M. Renson, Bull. Soc. Roy. Sci. Liege, 1973, 42, 129; (c) A. Tadino, L. Christiaens and M. Renson, Bull. Soc. Roy. Sci. Liege, 1973, 42, 146.
5. (a) I. D. Sadekov and V. Minkin, Advances in Heterocyclic Chemistry: Six-Membered Heterocycles with a Tellurium Atom, vol. 63, ed. A. R. Katritzky, Academic Press, Inc., London, 1995, pp. 1–60; (b) I. D. Sadekov, A. A. Ladatko, E. I. Sadekova, G. N. Dorofeenko and V. I. Minkin, Khim. Geterotsikl. Soedin., 1981, 343 (Chem. Abstr., 1981, 95, 80 692b); (c) M. R. Detty and B. J. Murray, J. Org. Chem., 1982, 47, 5235; (d) M. R. Detty and B. J. Murray, J. Am. Chem. Soc., 1983, 105, 883; (e) M. Detty and H. R. Luss, Organometallics, 1986, 5, 2250; (f) M. Detty, J. M. McKelvey and H. R. Luss, Organometallics, 1988, 7, 1131.
6. (a) H. Sashida, H. Kurahashi and Tsuchiya, J. Chem. Soc., Chem. Commun., 1991, 802; (b) H. Sashida, K. Ito and T. Tsuchiya, J. Chem. Soc., Chem. Commun., 1993, 1493; (c) H. Sashida, K. Ito and T. Tsuchiya, Chem. Pharm. Bull., 1995, 43, 19; (d) H. Sashida, K. Sadamori and T. Tsuchiya, Synth. Commun., 1998, 28, 713; (e) H. Sashida, Synthesis, 1998, 745; (f) H. Sashida and A. Kawamukai, J. Heterocycl. Chem., 1998, 35, 165.
7. J. Liu, M. Qui and X. Zhou, Synth. Commun., 1990, 20, 2759.
8. A. A. Bumber, E. P. Ivakhnenko, A. A. Ladatko, A. A. Arutyunyants, I. D. Sadekov and O. Yu. Okhlobistin, Khim. Geterotsikl. Soedin., 1988, 1196 (Chem. Abstr., 1989, 111, 38 699h).