Abstract
Previously unknown C60 fullerene-fused 1,4-oxathian-2-ones 1,9-[2′-oxo-1′,4′-oxathiano]-1,9-dihydro-(C60-Ih)[5,6]fullerene and 1,9-[3′-Methyl-2′-oxo-1′,4′-oxathiano]-1,9-dihydro-(C60-Ih)[5,6]fullerene were obtained by a selective reaction mercaptocarboxylic acids (mercaptoacetic and 2-mercaptopropionic) with fullerene epoxide C60O in the presence of NaOH in an inert atmosphere at room temperature under ultrasonication for 1 h. The yields of the target product were estimated at 96 and 87%, respectively (by HPLC). A plausible reaction mechanism for was proposed.
REFERENCES
Nakamura, E. and Isobe, H., Acc. Chem. Res., 2003, vol. 36, p. 807. https://doi.org/10.1021/ar030027y
Tzirakis, M.D. and Orfanopoulos, M., Chem. Rev., 2013, vol. 113, p. 5262. https://doi.org/10.1021/cr300475r
Echegoyen, L. and Echegoyen, L.E., Acc. Chem. Res., 1998, vol. 31, p. 593. https://doi.org/10.1021/ar970138v
Matsuo, Y., Chem. Lett., 2012, vol. 41, p. 754. https://doi.org/10.1246/cl.2012.754
Dennler, G., Scharber, M.C., and Brabec, C.J., Adv. Mater., 2009, vol. 21, p. 1323. https://doi.org/10.1002/adma.200801283
Miyauchi, H., Tanio, T., and Ohashi, N., Med. Chem. Lett., 1996, vol. 6, p. 2377. https://doi.org/10.1016/0960-894X(96)00435-0
Singh, A.K., Rai, A., and Yadav, L.D.S., Tetrahedron Lett., 2011, vol. 52, p. 3614. https://doi.org/10.1016/j.tetlet.2011.05.010
Kinzyabaeva, Z.S. and Sharipov, G.L., Ultrason. Sonochem., 2020, vol. 67, p. 105169. https://doi.org/10.1016/j.ultsonch.2020.105169
Kaufmann, H.P. and Schickel, R., Fette Seifen Anstrichm., 1963, vol. 65, p. 851. https://doi.org/10.1002/lipi.19630651017
Black, D.K., J. Chem. Soc. C, 1966, p. 1708. https://doi.org/10.1039/J39660001708
Orszulik, S.T., Tetrahedron Lett., 1986, vol. 27, p. 3781. https://doi.org/10.1016/S0040-4039(00)83879-4
Morgunova, V.A., Nikitina, L.E., Piemenkov, V.V., Fazlyeva, M.G., and Chugunov, Yu.V., Chem. Nat. Compd., 1999, vol. 35, p. 176. https://doi.org/10.1007/BF02234928
O’Sullivan, O.C.M., Collins, S.G., Maguire, A.R., Bohm, M., and Sander, W., Eur. J. Org. Chem., 2006, vol. 13, p. 2918. https://doi.org/10.1002/ejoc.200500971
Mandrus, D., Kele, M., Hettich, R.L., Guiochon, G., Sales, B.C., and Boatner, L.A., J. Phys. Chem. B, 1997, vol. 101, p. 123. https://doi.org/10.1021/jp962056e
Ko, W.B., Nam, J.H., and Hwang, S.H., Ultrasonics, 2004, vol. 42, p. 611. https://doi.org/10.1016/j.ultras.2004.01.083
Zhang, X., Gan, L., Huang, S., and Shi, Y., J. Org. Chem., 2004, vol. 69, p. 5800. https://doi.org/10.1021/jo0493368
Safaei-Ghomi, J. and Masoomi, R., Ultrason. Sonochem., 2015, vol. 23, p. 212. https://doi.org/10.1016/j.ultsonch.2014.08.004
Yinghuai, Z., Bahnmueller, S., Chibun, C., Carpenter, K., Hosmane, N.S., and Maguirec, J.A., Tetrahedron Lett., 2003, vol. 44, p. 5473. https://doi.org/10.1016/S0040-4039(03)01299-1
Yinghuai, Z., J. Phys. Chem. Solids, 2004, vol. 65, p. 349. https://doi.org/10.1016/j.jpcs.2003.08.027
Cataldo, F., Ursini, O., and Ragni, P., Plasma Chem. Plasma Process, 2013, vol. 33, p. 355. https://doi.org/10.1007/s11090-012-9417-5
Cataldo, F., Garcia-Hernandez, D.A., and Manchado, A., Fullerene Nanotube Carbon Nanostruct., 2014, vol. 22, p. 565. https://doi.org/10.1080/1536383X.2012.702160
Yoon, S., Hwang, S.H., and Ko, W.B., Curr. App. Phys., 2008, vol. 8, p. 774. https://doi.org/10.1016/j.cap.2007.04.022
Andrievsky, G.V., Kosevich, M.V., Vovk, O.M., Shelkovsky, V.S., and Vashchenko, L.A., J. Chem. Soc., Chem. Commun., 1995, p. 1281. https://doi.org/10.1039/C39950001281
Ko, W.B., Heo, J.Y., Nam, J.H., and Lee, K.B., Ultrasonics, 2004, vol. 41, p. 727. https://doi.org/10.1016/j.ultras.2003.12.029
Afreen, S., Muthoosamy, K., and Manickam, S., Ultrason. Sonochem., 2019, vol. 51, p. 451. https://doi.org/10.1016/j.ultsonch.2018.07.015
Afreen, S., Kokubo, K., Muthoosamy, K., and Manickam, S., RSC Adv., 2017, vol. 7, p. 31930. https://doi.org/10.1039/c7ra03799f
Kinzyabaeva, Z.S. and Sharipov, G.L., Ultrason. Sonochem., 2018, vol. 42, p. 119. https://doi.org/10.1016/j.ultsonch.2017.11.012
Sivakumar, M., Senthilkumar, P., Majumdar, S., and Pandit, A.B., Ultrason. Sonochem., 2002, vol. 9, p. 25. https://doi.org/10.1016/S1350-4177(01)00099-2
Manickam, S., Arigela, V.N.D., and Gogate, P.R., Fuel Proces. Technol., 2014, vol. 128, p. 388. https://doi.org/10.1016/j.fuproc.2014.08.002
Bulgakov, R. G., Kinzyabaeva, Z.S., Khalilov, L.M., and Yanybin, V.M., Russ. J. Org. Chem., 2010, vol. 46, p. 1776. https://doi.org/10.1134/s107042801012002x
Rabinovich, V.A. and Khavin, Z.Ya., Kratkii khimicheskii spravochnik (Concise Chemical Reference Book), Leningrad: Khimiya, 1991.
Isaacs, L., Wehrsig, A., and Diederich, F., Helv. Chim. Acta, 1993, vol. 76, p. 1231. https://doi.org/10.1002/hlca.19930760310
Elemes, Y., Silverman, S.K., Sheu, C., Kao, M., Foote, C.S., Alvarez, M.M., and Whetten, R.L., Angew. Chem. Int. Ed., 1992, vol. 31, p. 351. https://doi.org/10.1002/anie.199203511
Hirsch, A., Synthesis, 1995, vol. 8, p. 895. https://doi.org/10.1055/s-1995-4046
Kampe, K.-D., Egger, N., and Vogel, M., Аngew. Chem. Inr. Ed., 1993, vol. 32, p. 1174. https://doi.org/10.1002/anie.199311741
Parker, E. and Isaacs, N.S., Chem. Rev., 1959, vol. 59, p. 737. https://doi.org/10.1021/cr50028a006
ACKNOWLEDGMENTS
The structural studies were conducted at the “Agidel” Center for Collective Use, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences.
Funding
The work was funded by the Ministry for Education and Science of the Russian Federation in the framework of the State order (topic FMRS-2022-0077).
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Kinzyabaeva, Z.S. Ultrasound-Assisted Synthesis of C60 Fullerene-Fused 1,4-Oxathian-2-ones. Russ J Gen Chem 93 (Suppl 1), S131–S136 (2023). https://doi.org/10.1134/S1070363223140219
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DOI: https://doi.org/10.1134/S1070363223140219