574735-10-7Relevant academic research and scientific papers
Microwave-promoted insertion of Group 10 metals into free base porphyrins and chlorins: Scope and limitations
Dean, Michelle L.,Schmink, Jason R.,Leadbeater, Nicholas E.,Brueckner, Christian
, p. 1341 - 1345 (2008)
The scope and limitations of microwave heating as a tool for insertion of Group 10 metals into meso-tetraphenyl-porphyrin, -porpholactone, and -2,3-dihydroxychlorin derivatives are discussed. In some cases it is possible to reduce reaction times dramatically while obtaining good yields of the metallated products while in others new issues arise relating to the metal salt used as well as acceleration not only of the metallation reaction but also of byproduct formation. The Royal Society of Chemistry.
Expansion of a pyrrole in meso-tetraphenylporphyrin to a pyrazine imide moiety using a Beckmann rearrangement
Akhigbe, Joshua,Brueckner, Christian
, p. 3876 - 3884 (2013/07/19)
The group 10 metal complexes of β,β′-dioxoporphyrin monooxime 10M (M = NiII, PdII, PtII) are susceptible to a Beckmann rearrangement to produce the corresponding ring-expanded metallopyrazinoporphyrin imides 11M in good yields. These chromophores possess metallochlorin-like optical properties. Demetalation of the NiII complex furnishes the free-base porphyrinoid 11, which possesses a porphyrin-like optical spectrum. The monooximes are ultimately derived from meso-tetraphenylporphyrin, and the formal replacement of the porphyrin β,β′-double bond by an imide functionality is thus demonstrated. The imide functionality serves as a synthetic handle for further modification of the chromophore. A Beckmann reaction of a porphyrindione monooxime is used to expand a pyrrole to a pyrazine imide moiety within the porphyrin and generate a new pyrrole-modified porphyrin-like compound that contains a six-membered heterocycle. The imide functionality can serve as a synthetic handle for further manipulations of the chromophore. Copyright
