Decomposition of N-cyclopropyl-N-nitrosourea in the presence of reducing agents as a new way of generating the cyclopropyl radical |
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Authors: | Yu. V. Tomilov I. V. Kostyuchenko G. P. Okonnishnikova I. P. Klimenko E. V. Shulishov |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | A new way of generating cyclopropyl radicals in the base-catalyzed decomposition of N-cyclopropyl-N-nitrosourea in the presence of organic reducing agents (1-phenylpyrazolidin-3-one and 4-methoxyphenol) was developed. The cyclopropyl radical generated under these conditions can not only abstract a proton from the substrate to give cyclopropane but also form C-C or C-Br bonds in reactions with aromatic substrates or polybromomethanes. Dedicated to Academician O. M. Nefedov on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1934–1938, November, 2006. |
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Keywords: | cyclopropylnitrosourea cyclopropyldiazonium cyclopropyl radical cyclopropanes reducing agents NMR spectra |
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