ВЕСТНИК
Башкирского университета

ENGLISH
Главная Авторам Рецензентам Выпуски журнала Редколлегия Редакция Загрузить статью Подписка ISSN 1998-4812

Архив | Том 25, 2020, No. 3.

РЕАКЦИЯ [2+4]-ЦИКЛОПРИСОЕДИНЕНИЯ 2-МЕРКАПТОЭТАНОЛА К ФУЛЛЕРЕНУ С60 В ПРИСУТСТВИИ NAH ПОД ДЕЙСТВИЕМ УЛЬТРАЗВУКА

Вестник Башкирского университета. 2020. Том 25. №3. С. 506-511.
Download
  • © З. С. Кинзябаева

    Институт нефтехимии и катализа УФИЦ РАН

    Россия, Республика Башкортостан, 450075 Уфа, пр. Октября, 141

  • © А. М. Дмитриев

    Башкирский государственный университет

    Россия, Республика Башкортостан, 450076 г. Уфа, ул. Заки Валиди, 32

В реакции фуллерена С60 с 2-меркаптоэтанолом в присутствии NaH под действием ультразвука получен ранее неизвестный 1,4-оксатиановый аддукт фуллерена. Полученное соединение идентифицировано с использованием масс-(MALDI TOF/TOF), одно- и двумерной ЯМР 1Н, 13С (COSY, HSQC, HMBS), УФ-видимой спектроскопией.

Ключевые слова:

  • фуллерен С60
  • 1
  • 2-гидрокситиолы
  • ультразвук
  • гетероциклические соединения
  • fullerene С60
  • 1,2-hydroxythiols
  • ultrasound
  • heterocyclic compounds

ЛИТЕРАТУРА

  1. Nakamura E., Isobe H. Functionalized Fullerenes in Water. The First 10 Years of Their Chemistry, Biology, and Nanoscience // Acc. Chem. Res. 2003. Vol. 36. Pp. 807-815.
  2. Tzirakis M. D., Orfanopoulos M. Radical Reactions of Fullerenes: From Synthetic Organic Chemistry to Materials Science and Biology // Chem. Rev. 2013. Vol. 113. Pp. 5262-5321.
  3. Echegoyen L., Echegoyen L. E. Electrochemistry of Fullerenes and Their Derivatives // Acc. Chem. Res. 1998. Vol. 31. Pp. 593-601.
  4. Matsuo Y. Design Concept for High-LUMO-level Fullerene Electron-acceptors for Organic Solar Cells // Chem. Lett. 2012. Vol. 41. Pp. 754-759.
  5. Dennler G., Scharber M. C., Brabec C. J. Polymer-Fullerene Bulk-Heterojunction Solar Cells // Adv. Mater. 2009. Vol. 21. Pp. 1323-1338.
  6. Haubein A. H. New Organophosphorus Derivativesofp-Thioxaneand 2,6-Dimethyl-p-thioxane with Insecticidal and Acaricidal Activity // J. Am. Chem. Soc. 1959. Vol. 81(1). Pp. 144-148.
  7. Miyauchi H., Tanio T., Ohashi N. Synthesis and antifungal activity of new azole derivatives containing an oxathiane ring // Bioorg. Med. Chem. Lett. 1996. Vol. 6. Pp. 2377-2380.
  8. Kim J. W., Park H. B., Chung B. Y., Lee J. B., Cho J.-H., Oh C. H. Synthesis and Antibacterial Activity of 1β-Methyl-2- [5-(α,β-disubstituted ethyl)pyrrolidin-3-ylthio]carbapenem Derivatives. Part II // Bull. Korean Chem. Soc. 2006. Vol. 27. Pp. 1164-1170.
  9. Mandrus D., Kele M., Hettich R. L., Guiochon G., Sale B. C., Boatner L. A. Sonochemical Synthesis of C60H2 // J. Phys. Chem. B 1997. Vol. 101. Pp. 123-128.
  10. Ko W. B., Nam J. H., Hwang S. H. The oxidation of fullerene[C60] with various amine N-oxides under ultrasonic irradiation // Ultrasonics. 2004. Vol. 42. Pp. 611-615.
  11. Zhang X., Gan L., Huang S., Shi Y. Iodo-Controlled Selective Formation of Pyrrolidino[60]fullerene and Aziridino[60]fullerene from the Reaction between C60 and Amino Acid Esters // J. Org. Chem. 2004. Vol. 69. Pp. 5800-5802.
  12. Safaei-Ghomi J., Masoomi R. An efficient comparison of methods involving conventional, grinding and ultrasound conditions for the synthesis of fulleroisoxazolines // Ultrason. Sonochem. 2015. Vol. 23. Pp. 212-218.
  13. Yinghuai Z., Bahnmueller S., Chibun C., Carpenter K., Hosmane N.S., Maguirec J.A. An effective system to synthesize methanofullerenes: substrate-ionic liquid-ultrasonic irradiation // Tetrahedron Lett. 2003. Vol. 44. Pp. 5473-5476.
  14. Yinghuai Z. Application of ultrasound technique in the synthesis of methanofullerene derivatives // J. Phys. Chem. Solids. 2004. Vol. 65. Pp. 349-353.
  15. Cataldo F., Ursini O., Ragni P. Fullerene C60 Trichloromethylation Through CCl4 Plasmalysis or Sonolysis // Plasma Chem. Plasma Process. 2013. Vol. 33. Pp. 355-365.
  16. Cataldo F., Garcia-Hernandez D. A., Manchado A. Sonochemical Synthesis of Fullerene C60/Anthracene Diels-Alder Mono and Bis-adducts // Fullerenes, Nanotub. Carbon Nanostruct. 2014. Vol. 22. Pp. 565-574.
  17. Yoon S., Hwang S. H., Ko W. B. Cycloaddition of 2′-azidoethyl glycosides to fullerene[C60] under ultrasonic irradiation // Curr. App. Phys. 2008. Vol. 8. Pp. 774-777.
  18. Khakina E. A., Yurkova A. A., Peregudov A. S., Troyanov S. I., Trush V. V., Vovk A. I., Mumyatov A. V., Martynenko V. M., Balzarini J., Troshin P. A. Highly selective reactions of C60Cl6 with thiols for the synthesis of functionalized [60]fullerene derivatives // Chem. Commun. 2012. Vol. 48. Pp. 7158-7160.
  19. Takaguchi Y., Katayose Y., Yanagimoto Y., Motoyoshiya J., Aoyama H., Wakahara T., Maeda Y., Akasaka T. Photoinduced Dithiolation of Fullerene[60] with Dendrimer Disulfide // Chem. Lett. 2003. Vol. 32. Pp. 1124-1125.
  20. Iskin B., Yilmaz G., Yagci Y. Mono-addition Synthesis of Polystyrene-Fullerene (C60) Conjugates by Thiol-Ene Chemistry // Chem. Eur. J. 2012. Vol. 19. Pp. 10254-10257.
  21. Yang X., Huang S., Jia Z., Xiao Z., Jiang Z., Zhang Q., Gan L., Zheng B., Yuan G., Zhang S. Reactivity of fullerene epoxide: preparation of fullerene-fused thiirane, tetrahydrothiazolidin-2-one, and 1,3-dioxolane // J. Org. Chem. 2008. Vol. 73. Pp. 2518-2526.
  22. Duczeka W., Tittelbach F., Costisella B., Niclas H.-J. Reaction of [60]Fullerene with 5-Imino-1,2,4-tbiadiazolidine-3-ones: Formation of New C60-fused Heterocycles // Tetrahedron. 1996. Vol. 52. Pp. 8733-8738.
  23. Izquierdo M., Osuna S., Filippone S., Martín-Domenech A., Solà M., Martín N. On the Regioselective Intramolecular Nucleophilic Addition of Thiols to C60 // Eur. J. Org. Chem. 2009. Pp. 6231-6238.
  24. Li F.-B., Zhu Y.-F., Zhang X.-F., Shi J.-L., Wu J., Chen L., Liang X.-X., Liu L. Synthesis of oxazolidinofullerenes/thiazolidinofullerenes: novel reaction of [60] fullerene with isocyanates/isothiocyanates promoted by ferric perchlorate // RSC Adv. 2014. Vol. 4. Pp. 48085-48094.
  25. Wu S.-L., Gao X. Copper-Catalyzed Aerobic Oxidative Reaction of C60 with Aliphatic Primary Amines and CS2 // J. Org. Chem. 2018. Vol. 83. Pp. 2125-2130.
  26. Giesa S., Gross J. H., Hull W. E., Lebedkin S., Gromov A., Gleitera R., Krätschmer W. C120OS: the first sulfur-containing dimeric [60]fullerene derivative // Chem. Commun. 1999. Pp. 465-466.
  27. Ohno M., Kojima S., Eguchi S. Dihydrothiopyran-fused [60]Fullerene from Hetero-Diels-Alder Reaction with Thioacrylamide and Acyl Chloride // J. Chem. Soc., Chem. Commun. 1995. Pp. 565-566.
  28. Ohno M., Kojima S., Shirakawa Y., Eguchi S. Hetero-Diels-Alder Reaction of Fullerene: Synthesis of Thiochroman-Fused C60 with o-Thioquinone Methide and Oxidation to Its S-Oxides // Tetrahedron Lett. 1995. Vol. 36. Pp. 6899-6902.
  29. Cataldo F., Garcia-Hernandez D. A., Manchado A. Sonochemical Synthesis of Fullerene C60/Anthracene Diels-Alder Mono and Bis-adducts // Fullerenes, Nanotub. Carbon Nanostruct. 2014. Vol. 22. Pp. 565-574.
  30. Krautler B., Muller T., Duarte-Ruiz A. Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State // Chem. Eur. J. 2001. Vol. 7. Pp. 3223-3235.
  31. Kinzyabaeva Z. S., Sharipov G. L. A selective synthesis of the fullerene-fused dioxane adduct via heterogeneous reaction of C60 withα-diols and NaOH under ultrasonication // Ultrason. Sonochem. 2018. Vol. 42. Pp. 119-123.
  32. Isaacs L., Wehrsig A., Diederich F. Improved Purification of C60 and Formation of σ- and π-Homoaromatic methano-bridged fullerenes by reaction with alkyl diazoacetates // Helv. Chim. Acta 1993. Vol. 76. Pp. 1231-1250.
  33. Rubin Y., Khan S., Freedberg D. I., Yeretzian C. Synthesis and X-ray Structure of a Diels-Alder Adduct of C60 // J. Am. Chem. Soc. 1993. Vol. 115. Pp. 344-345.
  34. Elemes Y., Silverman S. K., Sheu C., Kao M., Foote C. S., Alvarez M. M., Whetten R. L. Reaction of C60 with Dimethyldioxirane-Formation of an Epoxide and a 1,3-Dioxolane Derivative // Angew. Chem., Int. Ed. Engl. 1992. Vol. 31. Pp. 351-353.

Copyright © Вестник Башкирского университета 2010-2023