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Geminal systems

48. Dialkoxyaminyl radicals and tetraalkoxyhydrazines

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

By oxidation of N,N-dialkoxyamines RONHOR′ (I), we obtained dialkoxyaminyl radicals (II) which are stable in solution and inert to O2, whose structure has been confirmed by an EPR study of photolysis of solutions of (I) in the presence of 2,6-di-tertbutyl-p-benzoquinone. The radicals of (II) exist in solution in equilibrium with their dimers: tetraalkoxyhydrazines (V), whose concentration increases when the solutions are cooled. In three cases (R=R′=Me, R= R′= t-BuCH2, R=Me, R′=i-Bu), hydrazines (V) are isolated in pure form. From the temperature dependence of the concentration of radicals (II), we determine the thermodynamic parameters for their equilibrium dimerization. Using the PMR method, we establish the pyramidal configuration of the N atoms in hydrazines (V).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1819–1825, August, 1989.

For previous communication, see [1].

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Prokof'ev, A.I., Rudchenko, V.F., Ignatov, S.M. et al. Geminal systems. Russ Chem Bull 38, 1666–1671 (1989). https://doi.org/10.1007/BF00956953

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  • DOI: https://doi.org/10.1007/BF00956953

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