Abstract
2,3-Dichloroprop-1-ene reacted with diphenyl disulfide in the system hydrazine hydrate-potassium hydroxide at 30–35°C to give three products: 2-chloro-3-phenylsulfanylprop-1-ene, 1-phenylsulfanylpropadiene, and 1-phenylsulfanylprop-1-yne. Variation of temperature ensures selective synthesis of one of the above products, which confirms their successive formation (domino reaction). The domino reaction at 60°C goes further to afford (Z)-1,2-bis(phenylsulfanyl)prop-1-ene.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Levanova, E.P., Grabel’nykh, V.A., Russavskaya, N.V., Klyba, L.V., Zhanchipova, E.R., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen. Chem., 2009, vol. 79, no. 6, p. 1097.
Levanova, E.P., Grabel’nykh, V.A., Russavskaya, N.V., Albanov, A.I., Elaev, A.V., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen. Chem., 2011, vol. 81, no. 7, p. 1560.
Levanova, E.P., Vshivtsev, V.Yu., Grabel’nykh, V.A., Sukhomazova, E.N., Russavskaya, N.V., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen. Chem., 2008, vol. 78, no. 10, p. 1980.
Deryagina, E.N., Russavskaya, N.V., Papernaya, L.K., Levanova, E.P., Sukhomazova, E.N., and Korchevin, N.A., Izv. Akad. Nauk, Ser. Khim., 2005, no. 11, p. 2395.
Deryagina, E.N., Korchevin, N.A., and Papernaya, L.K., Russ. J. Gen. Chem., 1997, vol. 67, no. 5, p. 812.
Acetylenes, Viehe, H.G., Ed., New York: Marcel Dekker, 1969.
Brownbridge, P., Hunt, P.G., and Warren, S., J. Chem. Soc. Perkin Trans. 1, 1986, no. 9, p. 1695.
Polyakova, A.A. and Khmel’nitskii, R.A., Mass-spektrometriya v organicheskoi khimii (Mass Spectrometry in Organic Chemistry), Leningrad: Khimiya, 1972.
Lebedev, A.T., Mass-spektrometriya v organicheskoi khimii (Mass Spectrometry in Organic Chemistry), Moscow: BINOM, 2003.
Filippova, A.Kh., Lyashenko, G.S., Kalikhman, I.D., Pestunovich, V.A., Nikol’skaya, S.A., and Voronkov, M.G., Zh. Org. Khim., 1976, vol. 12, no. 4, p. 756.
Parham, W.E. and Stright, P.L., J. Am. Chem. Soc., 1956, vol. 78, no. 18, p. 4783.
Aivazov, B.V., Petrov, S.M., Khairullina, V.R., and Yapryntseva, V.G., Fiziko-khimicheskie konstanty seraorganicheskikh soedinenii (Physicochemical Constants of Organosulfur Compounds), Moscow: Khimiya, 1964.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © E.P. Levanova, V.A. Grabel’nykh, A.V. Elaev, N.V. Russavskaya, L.V. Klyba, A.I. Albanov, O.A. Tarasova, N.A. Korchevin, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 7, pp. 1088–1092.
Rights and permissions
About this article
Cite this article
Levanova, E.P., Grabel’nykh, V.A., Elaev, A.V. et al. Domino reaction of 2,3-dichloroprop-1-ene with diphenyl disulfide in the system hydrazine hydrate-potassium hydroxide. Russ J Gen Chem 83, 1341–1344 (2013). https://doi.org/10.1134/S1070363213070074
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363213070074