Abstract
The reaction of 2-phenyl-gemdichlorocyclopropane or (2,2-dichlorocyclopropyl)benzene with ethyl alcohol in the presence of solid alkali gave phenylacrolein diethyl acetal or (2,2-diethoxy-1-methylethyl)benzene, which, upon subsequent dichlorocarbenation and transacetalization with ethylene glycol, formed 2-(2,2-dichloro-1-phenylcyclopropyl)-1,3-dioxolane. Thus, two approaches to the synthesis of a product simultaneously containing gem-dichlorocyclopropane and 1,3-dioxolane fragments have been proposed. It has been established that the best method is sequential dichlorocarbenation of [1-(di-ethoxymethyl)ethenyl]benzene and acetalization of the resulting product to form the target molecule: 2-(2,2-dichloro-1-phenylcyclopropyl)-1,3-dioxolane. The structure of the reaction products was confirmed by 1H and 13C NMR spectroscopy and chromato-mass spectrometry.
REFERENCES
Kukovinets, O.S., Nikolaeva, S.V., and Kunakova, R.V., Tsiklopropany (svoistva, sintez, primenenie) (Cyclopropanes: Properties, Synthesis, Application), Ufa: Gilem, 2006.
Raskil’dina, G.Z., Borisova, Yu.G., Yanybin, V.M., Sultanova, R.M., Spirikhin, L.V., and Zlotskii, S.S., Dokl. Chem., 2016, vol. 466, p. 8.
Zefirov, N.S., Kazimirchik, I.V., and Lukin, K.A., Tsikloprisoedinenie dikhlorkarbena k olefinam (Cycloaddition of Dichlorocarbene to Olefins), Moskva: Nauka, 1985.
Raskil’dina, G.Z., Valiev, V.F., and Zlotskii, S.S., Russ. J. Appl. Chem., 2016, vol. 89, no. 5, p. 753.
Brusentsova, E.A., Imashev, U.B., Molyavko, M.A., Zlotskii, S.S., Makara, N.S., and Zarudii, F.S., Bashkir. Khim. Zh., 2008, vol. 15, no. 1, p. 118.
Kazakova, A.N., Kuznetsov, V.M., Musavirova, L.R., Mikhailova, N.N., Bogomazova, A.A., Mudrik, V.P., and Zlotskii, S.S., Bashkir. Khim. Zh., 2013, vol. 20, no. 1, p. 8.
Mirakyan, S.M., Latypov, O.R., Dzhumaev, Sh.Sh., Raskil’dina, G.Z., Bugai, D.E., and Zlotskii, S.S., Bashkir. Khim. Zh., 2018, vol. 25, no. 1, p. 99.
Sukhonosova, E.V., Zlotskii, S.S., and Chanyshev, R.R., Bashkir. Khim. Zh., 2017, vol. 24, no. 1, p. 7.
Kletter, E.A., Ganiullina, E.R., Musavirov, O.R., Shiriazdanova, A.R., and Zlotskii, S.S., Bashkir. Khim. Zh., 2009, vol. 16, no. 1, p. 16.
Kazakova, A.N., Timofeeva, S.A., Yumakaeva, Yu.M., Khairullina, A.F., and Zlotskii, S.S., Bashkir. Khim. Zh., 2009, vol. 17, no. 4, p. 19.
Borisova, Yu.G., Raskil’dina, G.Z., and Zlotskii, S.S., Russ. J. Gen. Chem., 2016, vol. 86, no. 9, p. 2126.
Kostikov, R.R., Varakin, G.S., Molchanov, A.P., and Ogloblin, K.A., Russ. J. Org. Chem., 1996, vol. 32, no. 1, p. 25.
Aminova, E.K., Zlotskii, S.S., Kazakova, A.N., and Proskurnina, M.V., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2013, vol. 56, no. 6, p. 11.
Aminova, E.K., Kazakova, A.N., Mikhailova, N.N., Nizaeva, E.R., Baibulatov, V.D., and Zlotskii, S.S., Bashkir. Khim. Zh., 2013, vol. 20, no. 1, p. 28.
Aminova, E.K., Kazakova, A.N., Spirikhin, L.V., and Zlotskii, S.S., Dokl. Chem., 2013, vol. 451, p. 189.
Raskil’dina, G.Z., Valiev, V.F., Mirakyan, S.M., Chanyshev, R.R., and Zlotskii, S.S., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2017, vol. 60, no. 10, p. 16.
Valiev, V.F., Raskil’dina, G.Z., Ozden, I.V., Meshcheryakova, S.A., Spirikhin, L.V., and Zlotskii, S.S., Russ. J. Gen. Chem., 2017, vol. 87, no. 8, p. 1872.
Raskil’dina, G.Z., Borisova, Yu.G., Spirikhin, L.V., and Zlotskii, S.S., Russ. Chem. Bull., 2019, vol. 68, no. 11, p. 2092.
Kagabu, S. and Mizoguchi, S., Synthesis, 1996, vol. 3, p. 372.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Additional information
Translated by S. Avodkova
Rights and permissions
About this article
Cite this article
Sakhabutdinova, G.N., Raskil’dina, G.Z., Chanyshev, R.R. et al. Synthesis of gem-Dichlorocyclopropane Derivatives Containing 1,3-Dioxolane Fragments. rev. and adv. in chem. 12, 255–258 (2022). https://doi.org/10.1134/S263482762370006X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S263482762370006X