Abstract
9-Methyl-3,3a,4,5-tetrahydro-6H-thieno[2,3-b]thiocino[4,5-c]isoxazole and 9-hydroxyimino-2-methyl-7-methylene-6, 7,8,9-tetrahydro-5H-thieno[2,3-b]thiocine have been prepared for the first time by the oxidation of 2-ω-alkenylthio-3-thiophenecarbaldoximes with NaOCl. X-ray structural investigations of thieno[2,3-b]thiocine and 2-homomethallylthio-5-methyl-3-thiophenecarbaldoxime have been carried out.
Similar content being viewed by others
References
M. M. Krayushkin, M. A. Kalik, E. Yu. Zvezdina, and V. S. Bogdanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2837 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 2474 (Engl. Transl.)].
1,3-Dipolar cycloaddition Chemistry, Ed. A. Padwa, Intersci, New York, Chichester, Brisbane, Toronto, Singapore, 1984,1, 354.
M. M. Krayushkin, M. A. Kalik, and E. Yu. Zvezdina,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 247 [Bull. Acad. Sci. SSSR, Div. Chem. Sci, 1991,40, 228 (Engl. Transl.)].
L. Garanti, A. Sala and G. Zecchi,J. Org. Chem., 1975,40, 2403.
K. Tanaka, H. Masuda and K. Mitsuhashi,Bull. Chem. Soc. Japan, 1985,58, 2061.
J. Baran and H. Mayr,J. Org. Chem., 1989,54, 5012.
M. M. Krayushkin, M. A. Kalik, L. G. Vorontsova, E. Yu. Zvezdina, and M. G. Kurella,Mendeleev Commun., 1993, 114.
1,3-Dipolar cycloaddition Chemistry, Ed. A. Padwa, Intersci, New York, Chichester, Brisbane, Toronto, Singapore, 1984,1, 302.
R. P. Linstead and H. N. Ryddon,J. Chem. Soc., 1934, 1995.
O. S. Banot and P. C. Dutta,J. Chem. Soc., 1968, 2583.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1262–1266, July, 1993.
Rights and permissions
About this article
Cite this article
Krayushkin, M.M., Kalik, M.A., Vorontsova, L.G. et al. Synthesis and structure of novel derivatives of thieno[2,3-b]thiocine. An unusual product of intramolecular cycloaddition of 2-homomethallylthio-5-methyl-3-thiophenecarbonitrile oxide. Russ Chem Bull 42, 1204–1208 (1993). https://doi.org/10.1007/BF00702007
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00702007