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    SNAr Mechanism of Piperidine with 2,4-Dinitrobenzene & Meisenheimer Complex Synthesis

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    A) Write a detailed mechanism for the reaction of piperidine with 2,4-dinitrochlorbenzene.

    b) A "spiro" species has two rings that have one carbon atom in common. Outline a synthesis of the spiro Meisenheimer complex shown in the attachment, starting with 1-chloro-2,4,6-trinitrobenzene.

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    Solution Preview

    Piperidine, hexahydropyridine, is a family of heterocyclic organic compound derived from pyridine through hydrogenation. It has one nitrogen atom in the cycle. It is a clear liquid with pepper-like aroma. It boils at 106 C, soluble in water, alcohol, and ether. The major application of piperidine is for the production of Dipiperidinyl dithium tetrasulfide used as a rubber vulcanization accelerator. In pharmaceutical synthesis industry, it is used as a special solvent and a protecting group for peptide synthesis. Piperidine derivative compounds are used as intermediate to make crystal derivative of aromatic nitrogen compounds containing nuclear halogen atoms. Ring system compounds with nitrogen which have basic property play important roles as cyclic component in industrial field such as raw materials for hardener of epoxy resins, corrosion inhibitors, insecticides, accelerators for rubber, urethane catalysts, antioxidants and as a catalyst for silicone esters. They are used in manufacturing pharmaceuticals.

    Just some short facts on the compound to be complexed with the 2,4 dinitro-chlorbenzene. I also found for your enjoyment several links that are quite instructive. The first one, I believe is really very helpful in the theory: ...

    Solution Summary

    The solution provides a clue to the question of spiro species synthesis so that the reader can attempt to find the answer themselves before opening the attached document containing the detailed explanation of the mechanisms involved and how they occur.