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From the Principle of Areno‐Analogy to Heterocyclopolyaromatic Compounds
Author(s) -
Kauffmann Thomas
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197900013
Subject(s) - electrophile , chemistry , amide , ring (chemistry) , reactivity (psychology) , stereochemistry , linkage (software) , nucleophile , group 2 organometallic chemistry , analogy , medicinal chemistry , computational chemistry , combinatorial chemistry , molecule , organic chemistry , catalysis , medicine , biochemistry , alternative medicine , pathology , gene , linguistics , philosophy
Organometallic linkage of heteroaromatic compounds provided a means of synthesizing complicated combinations of heteroaromatic compounds; not only nucleophilic aromatic substitution, but also “ArCu/ArHal linkage”, “organometallic oxidative linkage”, and “metal amide linkage” have been employed. The heterocyclopolyaromatic compounds are made of one, two, or three kinds of heteroaromatic species as ring members. These syntheses illustrate the construction of heterocycles from large, performed structural units. Competition experiments showed that the reactivity typical of the individual species is enhanced in open‐chain combinations (Ar Nu ) n and (Ar E ) n (Ar Nu , Ar E : nucleo‐ and electrophilic heteroaromatic systems, respectively); the opposite situation is mostly encountered in the case of Ar Nu A E combinations.—Cycloocta[1,2‐ b :4,3‐ b ′5,6‐ b ″:8,7‐ b ‴]tetrathiophene, the only heterocyclopolyaromatic system yet to have been studied in detail, proved surprisingly inclined to undergo monosubstitution reactions.