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Conformational analysis of stereoisomers of 2,4-dimethyl-5-isopropyl-1,3,2-dioxaborinane

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Abstract

The investigation of conformation conversions of cis- and trans-isomers of 2,4-dimethyl-5-isopropyl-1,3,2-dioxaborinane using ab initio quantum-chemical approximation HF/6-31G(d) and the hybrid DFT-method PBE/3z showed that the routes of the transformations presuppose an equilibrium between sofa conformers with the different orientation of substituents at the atoms C4 and C5 of the ring that convert into each other through transition states corresponding to the equatorial and axial conformations of the 2,5-twist form. Based on experimental data of 1H NMR spectra and calculated vicinal spin-spin coupling constants the quantitative conformational composition of cis- and trans-isomers was established and also the ΔGo value of the conformation equilibrium was determined.

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References

  1. Gren’, A.I. and Kuznetsov, V.V., Khimiya tsiklicheskikh efi rov bornykh kislot (Chemistry of Cyclic Esters of Boric Acids), Kiev: Naukova Dumka, 1988, p. 160.; Rossi, K. and Pihlaya, K., Acta, Chem. Scand., 1985, 39B, p. 671; Matteson, D.S., J. Organometal. Chem., 1999, vol. 581, p. 51; Kliegel, W., Preu, L., Rettig, S.J., and Trotter, J., Can. J. Chem., 1986, vol. 64, p. 1855; Kuznetsov, V.V., Izv. Russ. Akad. Nauk, Ser. Khim., 2005, p. 1499; Kuznetsov, V.V., Uspekhi organicheskogo kataliza i khimii geterotsiklov (Achievements in Organic Catalysis and Chemistry of Heterocycles), Moscow: Khimiya, 2006, p. 336; Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Zh. Org. Khim., 2008, vol. 44, p. 783; Calow, A.D.J. and Whiting, A., Org. Biomol. Chem., 2012, vol. 10, p. 5485; Cid, J., Gulyas, H., Carbo, J.J., and Fernandez, E., Chem. Soc. Rev., 2012, vol. 41, p. 3558.

    Google Scholar 

  2. Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Khim. Geterotskl. Soedin., 2009, p. 925; Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Khim. Geterotsikl. Soedin., 2010, p. 1245; Valiakhmetova, O.Yu. and Kuznetsov, V.V., Zh. Obshch. Khim., 2008, vol. 78, p. 2007; Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Zh. Obshch. Khim., 2010, 80, p. 766.

    Google Scholar 

  3. Kuznetsov, V.V., Zh. Strukt. Khim., 2001, vol. 42, p. 591; Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Sovremennye naukoemkie tekhnologii (Modern High Technologies), 2006, vol. 2, p. 71.

    Google Scholar 

  4. Kuznetsov, V.V., Alekseeva, E.A., Khudyakov, V.V., and Levshov, Yu.A., Zh. Org. Khim., 2002, vol. 72, p. 429; Kuznetsov, V.V., Bochkor, S.A., and Spirikhin, L.V., Bash. Khim. Zh., 2000, vol. 7, p. 23; Kuznetsov, V.V. and Spirikhin, L.V., Zh. Strukt. Khim., 2000, vol. 41, p. 844.

    Google Scholar 

  5. HyperChem, 8.0. http://www.hyper.com.

  6. Laikov, D.N. and Ustynyuk, Yu.A., Izv. Russian Akad. Nauk, Ser. Khim., 2005, p. 804.

    Google Scholar 

  7. Kuznetsov, V.V., Khim. Geterotsikl. Soedin., 2002, p. 1453.

    Google Scholar 

  8. Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Zh. Obshch. Khim., 2009, vol. 79, p. 930.

    Google Scholar 

  9. Zefirov, N.S., Blagoveshchenskii, V.S., Kazimirchik, I.V., and Yakovleva, O.P., Zh. Org. Khim., 1971, vol. 7, p. 594.

    CAS  Google Scholar 

  10. Haasnoot, C.A.G., de Leeuw, F.A.A.M., and Altona, C., Tetrahedron, 1980, vol. 36, p. 2783.

    Article  CAS  Google Scholar 

  11. Huggins, M.L., J. Am. Chem. Soc., 1953, vol. 75, p. 4123.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Ufa State Aviation Technical University, Ufa, 45000, Russia

    V. V. Kuznetsov

  2. Ufa State Petroleum Technological University, Ufa, Russia

    V. V. Kuznetsov

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  1. V. V. Kuznetsov
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Correspondence to V. V. Kuznetsov.

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Original English Text © V.V. Kuznetsov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 2, pp. 304–308.

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Kuznetsov, V.V. Conformational analysis of stereoisomers of 2,4-dimethyl-5-isopropyl-1,3,2-dioxaborinane. Russ J Org Chem 49, 298–302 (2013). https://doi.org/10.1134/S1070428013020206

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  • DOI: https://doi.org/10.1134/S1070428013020206

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