- Straining strained molecules. III. The spectral and mutagenic properties and an alternate synthesis of diaceperylene and dicyclopentaperylene
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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.
- Mitchell, Reginald H.,Chaudhary, Mahima,Williams, Richard Vaughan,Fyles, Robert,Gibson, Jack,et al.
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p. 1015 - 1021
(2007/10/02)
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- Strained Perylenes By Clamping - The Coronene Isomer Dicyclopentaperylene and Dimethanoperylene
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Perylene (3) is clamped by C2 and C1 bridges with formation of the heptacyclic title compound dicyclopentaperylene (10) (characterized) and 1H,6H-dicyclobutaperylene (4) (detected by mass spectrometry and 1H NMR absorptions).The influence of strain on UV and fluorescence spectra and on cyclic voltammetry is discussed.
- Jaworek, Wilfried,Voegtle, Fritz
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p. 347 - 352
(2007/10/02)
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