Abstract
Sterically hindered, stable 3-thiophenecarbonitrile oxides containing electron-accepting groups (SO2R, Br) in the 2- or 4-position are converted to substituted 4,5-dithienylfuroxanes when boiled in benzene or toluene, whereas trialkyl-substituted 3-thiophenecarbonitrile oxides isomerize quantitatively to the corresponding isocyanates.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
C. Grundmann and P. Grünanger, The Nitrile Oxides, Springer-Verlag, Berlin (1971), p. 62.
M. M. Krayushkin, M. A. Kalik, V. K. Zav'yalova, V. S. Bogdanov, and A. A. Loktionov, Khim. Geterotsikl. Soedin., No. 12, 1620 (1989).
M. M. Krayushkin, A. A. Loktionov, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 8, 1034 [sic].
L. I. Khmel'nitskii, S. S. Novikov, and T. I. Godovikova, The Chemistry of Furoxanes (Structure and Synthesis) [in Russian], Nauka, Moscow (1981).
G. A. Taylor, J. Chem. Soc., Perkin 1, No. 6, 1181 [sic].
A. Rauk and P. F. Alewood, Can. J. Chem., 55, 1498 [sic].
C. Grundmann and P. Kochs, Angew. Chem. Int. Ed., 9, 635 (1970).
S. Shiraishi, T. Sigemoto, M. Miyahara, and S. Ogawa, Bull. Chem. Soc. Jpn., 54, 3863 (1981).
S. Morrochi, A. Ricca, A. Selva, and A. Zanarotti, Gazz. Chim. Ital., 99, 165 (1969).
M. M. Krayushkin, M. A. Kalik, V. K. Zav'yalova, and V. S. Bogdanov, Khim. Geterotsikl. Soedin., No. 3, 403 (1988).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 909–913, July, 1990.
Rights and permissions
About this article
Cite this article
Krayushkin, M.M., Kalik, M.A. & Loktionov, A.A. Effect of electronic factors on the dimerization and isomerization of substituted nitrile oxides of the thiophene series. Chem Heterocycl Compd 26, 756–760 (1990). https://doi.org/10.1007/BF00509702
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00509702