Abstract
The addition of selenium tetrabromide to the olefinic bond of N-substituted allylacetic acid amides (reagent molar ratio 2∶1) proceeds counter to Markownikoff's rule with the formation of tetrahydrofuran derivatives. The addition of tellurium tetrahalides under the same conditions (reagent molar ratio 1∶1) proceeds in accordance with Markownikoff's rule with the formation of tetrahydropyran derivatives.
Similar content being viewed by others
Literature Cited
V. G. Lendel, A. Yu. Sani, Yu. Yu. Migalina, B. I. Pak, and I. M. Balog, Khim. Geterotsikl. Soedin., No. 4, 564 (1989).
Yu. V. Migalina, I. V. Smolanka, V. I. Staninets, V. G. Lendel, and I. M. Balog, USSR Author's Certificate No. 450806; Byull. Izobret., No. 43, 59 (1974).
M. Ogawa and R. Ischioka, Bull. Chem. Soc. Jpn. 43, 496 (1970).
J. Bergman and L. Engman, J. Am. Chem. Soc., 103, 5196 (1981).
B. V. Ioffe, R. R. Kostikov, and V. V. Rozin, Physical Methods for the Determination of the Structures of Organic Molecules [in Russian], Leningrad State University, Leningrad (1976), p. 103.
Author information
Authors and Affiliations
Additional information
Communication 10 in the series “Electrophilic reactions of halides of elements of the sixth group”; see [1] for Communication 9.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 743–745, June, 1989.
Rights and permissions
About this article
Cite this article
Migalina, Y.V., Sani, A.Y., Balog, I.M. et al. Reactions of N-substituted allylacetic acid amides with selenium and tellurium tetrahalides. Chem Heterocycl Compd 25, 610–612 (1989). https://doi.org/10.1007/BF00470015
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00470015