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Cyclic π‐Conjugated Systems Annelated with Bicycloalkene Frameworks
Author(s) -
Komatsu Koichi
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199907)1999:7<1495::aid-ejoc1495>3.0.co;2-j
Subject(s) - chemistry , bicyclic molecule , conjugated system , annulation , redox , computational chemistry , stereochemistry , organic chemistry , polymer , catalysis
The present article gives an account of the synthesis and chemical properties of the cyclic π‐conjugated hydrocarbons annelated with bicyclic σ‐frameworks. Particular emphasis is placed on π‐systems carrying a positive charge, which is remarkably stabilized by complete annelation with bicyclo[2.2.2]octene. In such systems, not only the kinetic effects but also electronic effects due to σ‐π conjugation affect the properties of the π‐systems. The thermodynamic properties, redox behavior, and the X‐ray crystal structures are discussed.