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Nonadditive effects of structural factors in reactions of aryloxiranes with arenesulfonic acids. Observation of isoparametricity phenomenon

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Abstract

In reactions of aryloxiranes XC6H4(3)CH(O)CH2 with arenesulfonic acids YC6H4SO3H in a mixture of dioxane with diglyme (1: 1) at 265 K the nonadditive effects of substituents X and Y were strongly revealed, therefore it was possible to observe experimentally the isoparametricity phenomenon: In the isoparametric point σX IP = 1.42 with respect to the X substituent constant the rate of the oxirane ring opening did not depend on the structure of Y (ρY X = 0).

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References

  1. Lau, E.Y., Newby, Z.E., and Bruice, T.C. J. Am. Chem. Soc., 2001, vol. 123, p. 3350; Salomatina, O.V., Yarovaya, O.I., and Barkhash, V.A., Zh. Org. Khim., 2005, vol. 41, p. 167; Kas’yan, L.I., Kas’yan, A.O., and Okovityi, S.I., Zh. Org. Khim., 2006, vol. 42, p. 327; Yudin, A.K., Aziridines and Epoxides in Organic Synthesis, Weinheim: Wiley-VCH, 2006; Carlier, P.R., Deora, N., and Crawford, T.D., J. Org. Chem., 2006, vol. 71, p. 1592; Park, S.A., Lim, C.H., and Chung, K.-H., Bull. Korean, Chem. Soc., 2007, vol. 28, p. 1834; Zhao, Y. and Truhlar, D.G., J. Org. Chem., 2007, vol. 72, p. 295; Bespal’ko, Yu.N., Shved, E.N., and Oleinik, N.M., TEKh., 2008, vol. 44, p. 292; Fogassy, G., Pinel, C., and Gelbard, G., Catal. Commun., 2009, vol. 10, p. 557; Kas’yan, L.I. and Pal’chikov, V.A., Zh. Org. Khim., 2010, vol. 46, p. 7; Shpan’ko, I.V. and Sadovaya, I.V., TEKh., 2010, vol. 46, p. 171.

    Article  CAS  Google Scholar 

  2. Pal’m, V.A., Osnovy kolichestvennoi teorii organicheskikh reaktsii (Principles of Quantitative Theory of organic Reactions), Leningrad: Khimiya, 1977.

    Google Scholar 

  3. Shpanko, I.V., Sadovaya, I.V., and Kitaigorodskii, A.M., Mendeleev Commun., 2001, p. 83.

  4. Shpan’ko, I.V. and Sadovaya, I.V., TEKh., 2002, vol. 38, p. 116.

    Google Scholar 

  5. Dormer, J. and Moodie, R.B., J. Chem. Soc., Perkin Trans. II, 1994, p. 1195.

  6. Shpan’ko, I.V. and Sadovaya, I.V., Ukr. Khim. Zh., 2005, vol. 71, p. 60.

    Google Scholar 

  7. Kayser, M.M. and Morand, P., Can. J. Chem., 1980, vol. 58, p. 302; Shindo, M., Sugioka, T., and Shishido, K., Tetrahedron Lett., 2004, vol. 45, p. 9265; Solladie-Cavallo, A., Lupattelli, P., and Bonini, C., J. Org. Chem., 2005, vol. 70, p. 1605.

    Article  CAS  Google Scholar 

  8. Clotman, D., Muller, J.P., and Zeegers-Huyskens, T., Bull. Soc. Chim. Belg., 1970, vol. 79, p. 689.

    Article  CAS  Google Scholar 

  9. Shpan’ko, I.V., TEKh., 1999, vol. 35, p. 67; Shpan’ko, I.V., TEKh., 2001, vol. 37, p. 265; Shpanko, I.V., Kim, S.I., Koh, H.J, and Lee, I., Bull. Korean, Chem. Soc., 1995, vol. 16, p. 533.

    Google Scholar 

  10. Guss, C.O., J. Org. Chem., 1951, vol. 16, p. 887.

    Article  CAS  Google Scholar 

  11. Biggs, J., Chapman, N.B., Finch, A.F., and Wray, V., J. Chem. Soc. B, 1971, p. 55; Fuchs, R., and Vander Werf, C.A., J. Am. Chem. Soc., 1954, vol. 76, p. 1631.

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Authors and Affiliations

  1. Donetsk National University, Donetsk, 83001, Ukraine

    I. V. Shpan’ko, I. V. Sadovaya & N. V. Kulikova

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  1. I. V. Shpan’ko
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  2. I. V. Sadovaya
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  3. N. V. Kulikova
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Correspondence to I. V. Shpan’ko.

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Original Russian Text © I.V. Shpan’ko, I.V. Sadovaya, N.V. Kulikova, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 685–691.

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Shpan’ko, I.V., Sadovaya, I.V. & Kulikova, N.V. Nonadditive effects of structural factors in reactions of aryloxiranes with arenesulfonic acids. Observation of isoparametricity phenomenon. Russ J Org Chem 47, 687–693 (2011). https://doi.org/10.1134/S107042801105006X

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  • DOI: https://doi.org/10.1134/S107042801105006X

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