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Unusual formation of hydroperoxides in the reactions of substituted spiro[pyrazolinecyclopropanes]

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Abstract

3-Cyano- and 3-(alkoxycarbonyl)spiro[2-pyrazoline-5,1’-cyclopropane] and 5-phenylspiro[1-pyrazoline-3,1’-cyclopropane] undergo unusual transformations into 3(5)-substituted 5(3)-(2-hydroperoxyethyl)pyrazoles in the presence of atmospheric oxygen. The conditions for the formation of hydroperoxides (e.g., in oxygen-saturated solutions of spiro[2-pyrazoline-5,1’-cyclopropanes] in CHCl3) and their conversion into (2-hydroxyethyl)pyrazoles or the corresponding nitrates under the action of nitrosating reagents were considered.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    I. V. Kostyuchenko, G. P. Okonnishnikova, E. V. Shulishov & Yu. V. Tomilov

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  1. I. V. Kostyuchenko
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  2. G. P. Okonnishnikova
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  3. E. V. Shulishov
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  4. Yu. V. Tomilov
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2160–2164, October, 2004.

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Kostyuchenko, I.V., Okonnishnikova, G.P., Shulishov, E.V. et al. Unusual formation of hydroperoxides in the reactions of substituted spiro[pyrazolinecyclopropanes]. Russ Chem Bull 53, 2257–2261 (2004). https://doi.org/10.1007/s11172-005-0110-1

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  • DOI: https://doi.org/10.1007/s11172-005-0110-1

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