Reactions of N-(vinylimonophosphoranes) : Synthesis and properties of new aromatic compounds

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Preparation and thermal reactions of [(azulen-2-yl) imino] phosphorane and [(1-azaazulenyl) imino] phosphorane with 2-bromotropone afforded 6-aza-and 6,7-diazaazuleno [1,2-a] azulenes. The NMR and electronic spectral studies including PPP-type MO calculations of the compounds revealed that there are litle contribbution of peropheral 18-pi conjugation, but there are rather composed of two azulene-type pi-systems. The both compounds existing as cationic and dicationic species in acidic media were also studied. In relation to the studies, azuleno-[1,2-a] azulene was also prepared through the thermal reaction of 2H-cyclohepta [b]-furan-2-one with 2-(1-pyrrolidinyl)-3(2,4,6-cycloheptatrienlylpropene and subsequent hydride abstraction-deprotonation processes. The spectral data revealed also that the compound are composed of two azulene-type pi-systems, are agreeable with the theoretical predictions.Furthermore, diphenylphosphinyltroponeimine reacted with enolates to give 1-azaazalene derivatives. Furthear studies are underway in our laboratory to explore the scompe and generality of the methodology.