135904-98-2Relevant articles and documents
Synthesis and Properties of Acepleiadylene-1,2-dione
Suzuki, Seiichi,Tanaka, Shinri,Tsunetsugu, Josuke,Higashi, Miwako,Yamaguchi, Hiroyuki
, p. 1601 - 1635 (2007/10/02)
Acepleiadylene-1,2-dione (4) has been synthesized from cycloheptacenaphthene-1,2-dione (11) by bromination with NBS followed by dehydeobromination with triethylamine.Compound (11) was synthesized by Friedel-Crafts acylation of acepleiadane (10) with oxalyl chloride.Compound (10) was prepared from o-pleiadienequinone (6) by reduction with sodium borohydride to diols (7) and successive dehydration with low valent titanium.MNDO calculations indicated that compound (4) is nearly planar.The reduction potentials of dione (4) were determined by cyclic voltammetry which showed that E1 = -0.50 V and E2 = -0.84 V.Spectral and electrochemical data suggest that dione (4) is a annulenedione with a vinyl cross-link.