Dalton communications. Solvent-dependent forms of lithiated 5,5,10,10,15,15,20,20-octaethylporphyrinogen in solution and in the solid state and reaction with tetrahydrofuran

The fully lithiated form of 5,5,10,10,15,15,20,20-octaethylporphyrinogen (H-4L) synthesized in tetrahydrofuran (thf ) has been structurally characterized in its solvated form Li4L.3thf, while its unsolvated form from n-hexane behaves as a 'superbase' capable of decomposing thf to the lithium enolate identified in the aggregate Li6L(OCH=CH2)2.4thf.