Pathways of decomposition of N-cyclopropyl N nitrosoureas in methanol |
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Authors: | I. P. Klimenko Yu. V. Tomilov |
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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: | Decomposition of a series of N-cyclopropyl-N-nitrosoureas (CNU) in CD3OD was studied. These decompose much more rapidly than N-methyl-N-nitrosourea, one of the decomposition pathways being denitrosation, which is atypical of alkylnitrosoureas under the reaction conditions used. The nature of substituents in the cyclopropane ring has a great effect on the stability of CNU and the product ratio. In the presence of H2 SO4, decomposition occurs much more rapidly. Possible pathways of the formation of the major decomposition products of CNU are proposed based on the experimental data.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 359–370, February, 2005. |
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Keywords: | cyclopropylnitrosoureas denitrosation cyclopropanediazonium ion reaction mechanisms NMR spectra |
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