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Quantum chemical studies of mechanisms of organic reactions: VI. Reaction of ethane-1,2-dithiol with vinylidene chloride

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Abstract

A theoretical mechanism has been proposed for the reaction of vinylidene chloride with ethane-1,2-dithiol in the system hydrazine hydrate–potassium hydroxide on the basis of DFT quantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory. The reaction includes two consecutive stages: dehydrochlorination of vinylidene chloride to chloroacetylene and nucleophilic addition of one thiol group of ethane-1,2-dithiol to the β-carbon atom of chloroacetylene, followed by closure of 2,3-dihydro-1,4-dithiine ring via nucleophilic substitution of chlorine by sulfur atom of the second thiol group.

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References

  1. Chirkina, E.A., Mal’kina, A.G., Ushakov, I.A., and Krivdin, L.B., Russ. J. Org. Chem., 2016, vol. 52, p. 1267.

    Article  CAS  Google Scholar 

  2. Chirkina, E.A., Mal’kina, A.G., and Krivdin, L.B., Russ. J. Org. Chem., 2015, vol. 51, p. 313.

    Article  CAS  Google Scholar 

  3. Chirkina, E.A., Krivdin, L.B., Mal’kina, A.G., and Trofimov, B.A., Russ. Chem. Bull., Int. Ed., 2015, vol. 64, p. 511.

    Article  CAS  Google Scholar 

  4. Chirkina, E.A., Chernyshev, K.A., Krivdin, L.B., Potapov, V.A., and Amosova, S.V., J. Organomet. Chem., 2014, vol. 766, p. 49.

    Article  CAS  Google Scholar 

  5. Chirkina, E.A., Chernyshev, K.A., Pankrat’ev, E.Yu., Krivdin, L.B., Potapov, V.A., and Amosova, S.V., Russ. J. Org. Chem., 2013, vol. 49, p. 508..

    Article  CAS  Google Scholar 

  6. Levanova, E.P., Grabel’nyh, V.A., Vahrina, V.S., Albanov, A.I., Klyba, L.V., Russavskaya, N.V., and Korchevin, N.A., J. Sulfur Chem., 2014, vol. 35, p. 179.

    Article  CAS  Google Scholar 

  7. Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 820.

    Article  CAS  Google Scholar 

  8. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J. Gaussian 09, Revision C.01, Wallingford CT, Gaussian, 2009.

    Google Scholar 

  9. González, C. and Schlegel, H.B., J. Phys. Chem., 1990, vol. 94, p. 5523.

    Article  Google Scholar 

  10. González, C. and Schlegel, H.B., J. Chem. Phys., 1991, vol. 95, p. 5853.

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    E. A. Chirkina, E. P. Levanova & L. B. Krivdin

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  1. E. A. Chirkina
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  2. E. P. Levanova
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  3. L. B. Krivdin
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Correspondence to E. A. Chirkina.

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Original Russian Text © E.A. Chirkina, E.P. Levanova, L.B. Krivdin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 7, pp. 974–983.

For communication V, see [1].

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Chirkina, E.A., Levanova, E.P. & Krivdin, L.B. Quantum chemical studies of mechanisms of organic reactions: VI. Reaction of ethane-1,2-dithiol with vinylidene chloride. Russ J Org Chem 53, 986–994 (2017). https://doi.org/10.1134/S1070428017070053

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  • DOI: https://doi.org/10.1134/S1070428017070053

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