Azulene, Reactivity, and Scientific Interest Inversely Proportional to Ring Size; Part 1: The Five-Membered Ring

Abstract

The lack of azulene symmetry with respect to the axis perpendicular to a molecule creates an asymmetry of the electronic system, increasing the charge density of the five-atom ring and favoring its electrophilic substitutions. The increased reactivity of this ring has contributed to ongoing interest about the syntheses in which it is involved. The aim of this review is to present briefly and mainly in the form of reaction schemes the behavior of this system. After a short chapter that includes the research until 1984, subsequent research is presented as generally accepted chapters and subchapters to describe the behavior of the azulene system: metal free catalyst reactions; reactions catalyzed by metals; various azulene five-ring substitutions. The author insists on reaction yields, and in some cases considers it useful to present the proposed reaction mechanisms.

Designing potentially singlet fission materials with an anti-Kasha behaviour

“…Ideally, the electrophiles/nucleophiles used should be in excess to obtain the polysubstituted compounds. 62,63…”

Azulene, Reactivity, and Scientific Interest Inversely Proportional to Ring Size; Part 2: The Seven-Membered Ring

“…The chemical behavior of the azulene five-atom ring was the target of the first part of this review [1]. It was shown there that, unlike naphthalene which is symmetrical with respect to both axes, x and y, azulene is asymmetric with respect only to the y axis (Scheme 1).…”