Abstract
Stable 2-alkylthio- and 2-alkylsulfonylthiophene-3-carbonitrile oxides that contain various functional groups in the 4 and 5 positions of the thiophene ring (Br, OCH3, SCH3, SO2CH3) were synthesized. It is shown that the introduction of electron-acceptor substituents into any position of the ring of thiophene-3-carbonitrile oxides gives rise to acceleration of cycloaddition to styrene. The reactivities of o-substituted thiophene-3-carbonitrile oxides of the thiophene series in 1,3-dipolar cycloaddition reactions are determined by the overall effect of the electronic and steric factors of the substituents.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
Ch. Grundmann and P. Grünanger, The Nitrile Oxides, Springer-Verlag, Berlin-Heidelberg-New York (1971).
P. Beltrame, A. Comotti, and C. Veglio, Chem. Commun., No. 9, 996 (1967).
A. Dondoni, A. Mangini, and S. Chersetti, Tetrahedron Lett., No. 48, 4789 (1966).
C. Grundmann and J. M. Dean, J. Org. Chem., 30, 2809 (1965).
C. Grundmann and R. Richter, J. Org. Chem., 32, 2308 (1967).
C. Grundmann and R. Richter, J. Org. Chem., 33, 476 (1968).
A. Battaglia and A. Dondoni, Ric. Sci., 38, 201 (1968).
A. Dondoni and G. Barbaro, J. Chem. Soc., Perkin 2, No. 8, 1769 (1973).
P. Beltrame and G. Gelli, J. Heterocycl. Chem., 23, 1539 (1986).
J. Ywakura, K. Uno, S. Shiraishi, and T. Hongu, Bull. Chem. Soc. Jpn., 41, 2954 (1968).
M. M. Krayushkin, A. A. Loktionov, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 8, 1034 (1988).
M. M. Krayushkin, M. A. Kalik, V. K. Zav'yaloa, and V. S. Bogdanov, Khim. Geterotsikl. Soedin., No. 3, 403 (1988).
Ya. L. Gol'dfarb and M. A. Kalik, Khim. Geterotsikl. Soedin., No. 3, 475 (1969).
Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1769 (1969).
Ya. L. Gol'dfarb, M. A. Kalia, and M. L. Kirmalova, Zh. Obshch. Khim., 30, 1012 (1960).
Ya. L. Gol'dfarb, M. A. Kalik, and V. K. Zav'yalova, Khim. Geterotsikl. Soedin., No. 2, 182 (1981).
Ya. L. Gol'dfarb, M. A. Kalik, and V. K. Zav'yalova, Zh. Org. Khim., 15, 1540 (1979).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1620–1628, December, 1989.
Rights and permissions
About this article
Cite this article
Krayushkin, M.M., Kalik, M.A., Zav'yalova, V.K. et al. Synthesis of polyfunctional stable nitrile oxides of the thiophene series and their relative reactivities in 1,3-dipolar cycloaddition with styrene. Chem Heterocycl Compd 25, 1349–1355 (1989). https://doi.org/10.1007/BF00473862
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00473862