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Please note that the content of this book primarily consists of articles available from Wikipedia or other free sources online. High Quality Content by WIKIPEDIA articles! Nitrosobenzene is the organic compound with the formula C6H5NO. The compound can be viewed as hybrid of singlet O2 and azobenzene. This diamagnetic species exists in equilibrium with its dimer. The modern synthesis entails reduction of nitrobenzene to phenylhydroxylamine, C6H5NHOH, which is then oxidized by Na2Cr2O7. C6H5NO can also be prepared by oxidation of aniline using peroxymonosulfuric acid, Caro's acid. It is usually purified by steam distillation, where it comes over as a green liquid that solidifes to a colorless solid. The monomer undergoes Diels-Alder reactions with dienes. Condensation with anilines affords azobenzene derivatives (Mills reaction). Reduction of PhNO produces C6H5NH2. Most characteristically nitrosobenzene condenses with active methylene groups, e.g. of malonic esters, benzyl cyanide etc. For example, condensation with benzylcyanide PhCH2CN gives the imine PhC(CN)=NPh (The Ehrlich-Sachs Reaction).

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