1400678-83-2Relevant academic research and scientific papers
Meso-Tetraphenylporphyrin-derived oxypyriporphyrin, oxypyrichlorin, and thiomorpholinochlorin, as their Ni(II) complexes
Banerjee, Subhadeep,Zeller, Matthias,Brückner, Christian
, p. 576 - 588 (2012)
trans-Diolchlorin was prepared by nucleophilic addition of methyl-Grignard bromide to meso-tetraphenyl-2,3-dioxoporphyrin, as its free base or Ni(II) complex. The trans-configuration of the vic-diol functionality was shown by single crystal X-ray diffractometry. The nickel complex of the trans-dimethyldiol proved susceptible to Pb(IV) acetate-induced, oxidative diol cleavage, generating a meso-tetraphenylsecochlorin bismethylketone Ni(II) complex, the first example of this chromophore class. Under Br?nsted- basic conditions, this bisketone cyclized via an intramolecular aldol condensation to provide a meso-tetraphenyloxypyriporphyrin. Reduction of this porphyrin analog saturated the double bond in the pyridinone moiety, generating an oxypyrichlorin. Reaction of the meso-tetraphenylsecochlorin bismethylketone Ni(II) complex with Lawesson's reagent induced the formation of a thiomorpholinochlorin substituted with two methylene groups, the first example of any porphyrin analog containing a thiomorpholine moiety.
