Synthesis of a Polycyclic .PI.-Conjugated System Containing an Azulene Unit by the Flash Vacuum Pyrolytic Method. III. Synthesis and Properties of 4-Hydroxy-3H-cyclopent(a)azulen-3-one.

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  • Synthesis of a Polycyclic π-Conjugated System Containing an Azulene Unit by the Flash Vacuum Pyrolytic Method. III. Synthesis and Properties of 4-Hydroxy-3<i>H</i>-cyclopent[<i>a</i>]azulen-3-one

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4-Hydroxy-3H-cyclopent[a]azulen-3-one, a new tricyclic π-conjugated system containing a hydroxyazulene unit and a cyclopentadienone moiety, was synthesized by the application of flash vacuum pyrolysis in the final step. All the proton magnetic resonances of the compound shifted up-field compared with those of the referenced 1,2-dihydro compound in terms of an induced paramagnetic ring current in the periphery of this molecule. The characteristic prototropic tautomerization of 4-hydroxyazulenes was not observed in this system.

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