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31.21.1.43 Method 43: Substitution of Hydrogen Using Nitrogen Dioxide with Ozone: “Kyodai” Nitration

DOI: 10.1055/sos-SD-031-01277

Aitken, K. M.; Aitken, R. A.Science of Synthesis, (2007311242.

Kyodai nitration, which uses nitrogen dioxide and ozone, is named after the University of Kyoto where it was discovered and was first reported in 1991;[‌230‌] the developers of the method have published detailed reviews of the reaction.[‌231‌,‌232‌] Kyodai nitration is suitable for all aromatic compounds, from activated to deactivated, including water- and acid-sensitive substrates. A selection of successfully nitrated aromatic compounds is collected in Table 13, which also shows how the reaction conditions have been tuned according to the reactivity of the compound.[‌230‌,‌233‌‌242‌] Most of these examples are of simple aromatic compounds that were used in the development of the method, but the mildness of the reaction conditions mean it can also be used for large polyfunctional molecules. An account of some side reactions that occur in Kyodai nitration is found at the end of this section.

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References


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