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Synthesis 1977; 1977(4): 217-238
DOI: 10.1055/s-1977-24328
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Side-Reactions in Aromatic Nitration; Some Synthetic Aspects1

Hitomi SUZUKI*
  • *Department of Chemistry, Hiroshima University, Hiroshima 730, Japan
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Publication Date:
04 April 2002 (online)

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Aromatic compounds undergo three different types of reaction with nitrating agents under ionic conditions; (a) replacement by a nitro group of an atom or a group from a ring position (ordinary nitration), (b) reaction on a substituent group, and (c) addition reaction followed by various transformations. The present survey is directed towards the latter two types of reaction which have been a subject of continuing interest in recent years. 1. Side-Chain Nitrooxylation 1.1. Polyalkylbenzenes 1.2. Halogen Derivatives of Polyalkylbenzenes 1.3. Carboxy, Cyano, and Nitro Derivatives of Polyalkylbenzenes 1.4. Polyalkylphenols, Polyalkylphenyl Ethers and Polyalkylacetanilides 2. Side-Chain Nitration 3. Acetoxylation, Acetamidation, and Alkoxylation on Alkyl Side-Chains 4. Displacement Reactions on the Lateral Nitrogen and Oxygen Atoms 5. Formation of Addition Products 6. Acetoxylation and Alkoxylation 7. Oxynitration 8. Formation of Carbonyl Compounds 8.1. Cyclohexanones and Cyclohexadienones 8.2. Quinones 8.3. Benzaldehydes 9. Nitrative Coupling 10. Nitration with Rearrangement 11. Addenda