Proton-initiated conversion of dithiocarbamate derivatives of the 9,10-anthracenedione under conditions of acid-catalyzed cyclodehydration using the action of a mixture of H2SO4-AcOH and further treatment with perchloric acid was investigated. Based on the data of the spectral methods (1H, 13C NMR, IR, UV spectroscopy), it is established that the reaction stops at the stage of protonation of the sulfur atom of the thiocarbonyl group with the formation of perchlorates. The UV spectra of the obtained perchlorates are characterized by a hypochromic shift with a clearly pronounced absorption maximum.
[1] Gorelik M.: Khimiya Antrakhinonov i ikh Proizvodnykh. Khimiya, Moskva 1983.
[2] Malik E., Müller C.: Med. Res. Rev., 2016, 36, 705. https://doi.org/10.1002/med.21391
[3] Baqi Y., Müller C.: Tetrahedron Lett., 2012, 53, 6739. https://doi.org/10.1016/j.tetlet.2012.09.011
[4] Aly A., Brown A., Bedai T., Ishak E.: J. Sulfur Chem., 2012, 33, 605. https://doi.org/10.1080/17415993.2012.718349
[5] Zvarych V., Stasevych M., Lunin V. et al.: Monatsh. Chem., 2016, 147, 2093. https://doi.org/10.1007/s00706-016-1839-y
[6] Zvarych V., Stasevych M., Lunin V. et al.: Rus. J. Gen. Chem., 2016, 86, 2699. https://doi.org/10.1134/S1070363216120227
[7] Halenova T., Nikolaeva I., Stasevych M. et al.: Res. J. Pharm. Biol. Chem. Sci., 2017, 8, 1626.
[8] Stasevych M., Zvarych V., Lunin V. et al.: SAR QSAR Environ. Res., 2017, 28, 355.
https://doi.org/10.1080/1062936X.2017.1323796
[9] Bahrin L., Jones P., Hopf H.: Beilstein J. Org. Chem., 2012, 8, 1999. https://doi.org/10.3762/bjoc.8.226
[10] Lungu N., Bahrin L., Asaftei I. et al.: Rev. Chim. (Bucharest), 2014, 65, 181.
[11] Kratochvil N., Nepras M.: Collect. Czechoslovak Chem. Comm. 1972, 37, 1533. https://doi.org/10.1135/cccc19721533
[12] Bahrin L., Luca A., Birsa L.: Rev. Chim. (Bucharest), 2014, 65, 199.
[13] Axhausen J., Ruhl G., Kornath A.: Z. Naturforsch., 2012, 67b, 1235. https://doi.org/10.5560/ZNB.2012-0232
[14] Vandebeek R., Joris S., Aspila K., Chakraba C.: J. Can. Chem., 1970, 48, 2204. https://doi.org/10.1139/v70-368
[15] Shankaranarayana M., Patel C.: Acta Chem. Scand., 1965, 19, 1113. https://doi.org/10.3891/acta.chem.scand.19-1113