Porphyrazinediols: Synthesis, characterization, and complexation to group IVB metallocenes

The first metalated porphyrazinediols 11 have been prepared from (L)-(+)-di methyl tartrate via conversion into the corresponding dispoke or 2,3-dimeth oxy-2,3-butanediyl protected 2,3-dihydroxymaleonitrile, Linstead macrocycli zation, transmetalation, and deprotection. Their stability is very dependen t on the nature of the metal ion in the cavity of the porphyrazine. Reactio n of these porphyrazinediols with metallocene dichlorides led to new solita ire porphyrazines 12 while DDQ oxidation followed by trapping with diaminom aleonitrile afforded new porphyrazine dinitriles 14.