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Pyrrole was first detected by F. F. Runge in 1834, as a constituent of coal tar. [8] In 1857, it was isolated from the pyrolysate of bone. Its name comes from the Greek pyrrhos (πυρρός, "reddish, fiery"), from the reaction used to detect it—the red color that it imparts to wood when moistened with hydrochloric acid. [9]
This difference is partly related to the lower symmetry of the individual pyridine molecule (C 2v vs D 6h for benzene). A trihydrate (pyridine·3H 2 O) is known; it also crystallizes in an orthorhombic system in the space group Pbca, lattice parameters a = 1244 pm, b = 1783 pm, c = 679 pm and eight formula units per unit cell (measured at 223 K).
Pyridynes are the class of reactive intermediates derived from pyridine. Two isomers exist, the 2,3-pyridine (2,3-didehydropyridine) and the 3,4-pyridyne (3,4-didehydropyridine). The reaction of 3-bromo-4-chloropyridine with furan and lithium amalgam gives 1,4-epoxy-dihydroquinoline through the 2,3-pyridyne intermediate.
Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinoline, benzothiophene, indole, and benzofuran, respectively. The fusion of two benzene rings gives rise to a third ...
Heterocycles are often activated towards cation–π binding when the lone pair on the heteroatom is in incorporated into the aromatic system (e.g. indole, pyrrole). Conversely, when the lone pair does not contribute to aromaticity (e.g. pyridine), the electronegativity of the heteroatom wins out and weakens the cation–π binding ability.
Typical simple aromatic compounds are benzene, indole, and pyridine. [1] [2] Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene.
The reaction is carried out in the liquid phase in a continuous tube- or tube bundle reactor, which is operated in the cycle gas method. The catalyst is arranged as a fixed-bed and the conversion is carried out in the downflow mode. The product is obtained after multistage purification and separation by extractive and azeotropic distillation. [5]
The reaction employs an organic acidic medium such as acetic acid or propionic acid as typical reaction solvents. Alternatively p-toluenesulfonic acid or various Lewis acids can be used with chlorinated solvents. The aldehyde and pyrrole are heated in this medium to afford modest yields of the meso tetrasubstituted porphyrins [RCC 4 H 2 N] 4 H 2.