Abstract
A preparative procedure for the synthesis of thietanes bearing alkyl substituents in the β-position was developed. Using this procedure, 3-substituted thietanes can be obtained in four steps with an ultimate yield of > 50%. 3-R-thietanes (where R = CH3, C4H9, C5H11, C6H13, C6H5) and the corresponding sulfoxides and sulfones were synthesized and examined. The feasibility of preparation of gem-3,3-substituted thietanes was exemplified by the synthesis of 3,3-dihexylthietane.
Similar content being viewed by others
References
B. K. Clapperton, E. O. Minot, and D. R. Crump, J. Chem. Ecol. 15, 291 (1989).
R. D. Adams, J. L. Perrin, J. A. Queisser, and R. D. Rogers, J. Organomet. Chem. 596, 115 (2000).
N. A. Akperov, Neftepererab. Neftekhim., No. 1, 44 (2004).
Y. N. Romashin, T. H. Liu, B. T. Hill, and M. S. Platz, Tetrahedron Lett. 44, 6519 (2003).
W. O. Siegl and C. R. Johnson, J. Org. Chem. 35, 3657 (1970).
Synthesis and Properties of Organic Sulfur Compounds, Ed. by L. I. Belen’kii (Khimiya, Moscow, 1998) [in Russian].
M. Sander, Chem. Rev. 66, 341 (1966).
D. C. Dittmer and T. C. Sedergran, in Small Ring Heterocycles, Ed. by A. Hassner (Wiley, New York, 1985), Part III, p. 431.
Y. Etienne and R. Soulas, in Heterocyclic Compounds with Three and Four Membered Rings, Ed. by A. Weissberger (Wiley, New York, 1964), p. 685.
E. Block, in Comprehensive Heterocyclic Chemistry, Ed. by A. R. Katritzky (Pergamon, 1976), Vol. 7,Part 5, p. 403.
N. P. Volynskii and S. E. Shevchenko, Neftekhimiya 47, 125 (2007) [Pet. Chem. 47, 109 (2007)].
N. P. Volynskii, Neftekhimiya 43, 380 (2003) [Pet. Chem. 43, 344 (2003)].
Organic Syntheses, Collective Volume 1 ed. by H. Gilman et al. (Wiley, New York, 1942; Inostrannaya Literatura, Moscow, 1949).
Properties of Organic Compounds: A Handbook, Ed. by A. A. Potekhin (Khimiya, Leningrad, 1984) [in Russian].
N. G. Gaylord, Reduction with Complex Metal Hydrides (Interscience, New York, 1956; Inostrannaya Literatura, Moscow, 1959).
N. P. Volynskii, L. I. Perepelitchenko, and L. A. Zegel’man, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2506 (1987).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © S.E. Shevchenko, N.P. Volynskii, 2008, published in Neftekhimiya, 2008, Vol. 48, No. 2, pp. 123–128.
Rights and permissions
About this article
Cite this article
Shevchenko, S.E., Volynskii, N.P. Synthesis of 3-alkyl(aryl)thietanes. Pet. Chem. 48, 123–128 (2008). https://doi.org/10.1134/S0965544108020084
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0965544108020084