Unusual formation of hydroperoxides in the reactions of substituted spiro[pyrazolinecyclopropanes] |
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Authors: | I V Kostyuchenko G P Okonnishnikova E V Shulishov Yu V Tomilov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | 3-Cyano- and 3-(alkoxycarbonyl)spiro2-pyrazoline-5,1’-cyclopropane] and 5-phenylspiro1-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 spiro2-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.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2160–2164, October, 2004. |
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Keywords: | spiro[1- and 2-pyrazolinecyclopropanes] hydroperoxides opening of the cyclopropane ring organic nitrates |
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