Synthesis and properties of cyclohepta[fg]naphth[2,3-a]acenaphthylene-5,12-dione (naphth[2,3-h]acepleiadylene-5,12-dione)

Abstract

Naphth [2,3-h]acepleiadylene-5,12-dione (4) has been synthesized by the cycloaddition of acepleiadylene-5,8-dione (2) and o-dibromoquinodimethane generated in situ from 1,2-bis(dibromomethyl)benzene and sodium iodide. On the basis of their reduction potentials, determined by cyclic voltammetry, compound (4) and benz[h]acepleiadylene-5,10-dione (3) were shown to be [22]- and [18]-annulenediones, respectively. An unsuccessful attempt to synthesize naphth[2,3-h]acepleiadylene (7) is also described.