80879-80-7Relevant articles and documents
Straining strained molecules. III. The spectral and mutagenic properties and an alternate synthesis of diaceperylene and dicyclopentaperylene
Mitchell, Reginald H.,Chaudhary, Mahima,Williams, Richard Vaughan,Fyles, Robert,Gibson, Jack,et al.
, p. 1015 - 1021 (2007/10/02)
The synthesis of diaceperylene (1) from 5,6-dilithioacenaphthene via nickel or cobalt catalysed couplings proceeded in better yield than a multistep synthesis involving formation of 5,5'-diacenaphthene first.Dehydrogenation of 1 to dicylopentaperylene (2) proved a better route than coupling of 5,6-disubstituted acenaphthylene derivatives.Ultraviolet, proton, and carbon nuclear magnetic resonance spectra and electrode reduction potential data of 1 and 2 are discussed with respect to molecular mechanics calculations of strain in these and related bridged naphthalenes.Both 1 and 2 were found to be weakly mutagenic in an Ames microsome test, in contrast to cyclopentapyrene.