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Expansion by contraction: diversifying the photochemical reactivity scope of diazo-oxochlorins toward development of in situ alkylating agents.
- Tillmann Koepke, M. Pink, J. Zaleski
- Chemistry, BiologyJournal of the American Chemical Society
- 31 October 2008
The ability of these chromophores to photochemically react under substrate control may make unimolecular porphyrinoid photoreagents such as these useful for applications in photobiology or O2-independent photodynamic therapy.
Elucidation of the extraordinary 4-membered pyrrole ring-contracted azeteoporphyrinoid as an intermediate in chlorin oxidation.
Reaction of 2,3-dioxochlorins with benzeneselenic anhydride (BSA) results in the formation of unusual ring-contracted azetine derivatives that further react with BSA to afford porpholactones.
Gating the mechanistic pathway to the elusive 4-membered ring azeteoporphyrin.
- D. Dye, Tillmann Koepke, Raghunath O. Ramabhadran, K. Raghavachari, J. Zaleski
- ChemistryJournal of the American Chemical Society
- 2 August 2011
A model is presented showing that azeteoporphyrin formation via the Wolff rearrangement is dependent upon the structural disposition of the adjacent framework, and the specific reaction intermediate formed is very sensitive to this feature.
Expansion and contraction: Shaping the porphyrin boundary via diradical reactivity
Diazo-containing molecular constructs as potential anticancer agents: from diazo[b]fluorene natural products to photoactivatable diazo-oxochlorins.
Synthetic advances have now made diazo activation through visible region photolysis possible, and have led to characterization of a range of remarkable molecular photoproducts including azeteoporphyrinoids and O-H/N-H insertion products.
Photochemical preparation of pyrrole ring-contracted chlorins by the Wolff rearrangement.
Photolysis of the Ni(II), Cu(II), and Zn(II) 2-diazo-3-oxochlorins generates 4-membered rings containing azeteoporphyrins.
A Facile Synthesis of 2-Diazo-3-oxochlorins by Lewis Acid Activation: Selective Modification of π-Electron Conjugated Macrocycles
We report a new and direct synthesis of 2-diazo-3-oxochlorins [M = 2 H, Ni(II), Cu(ll), Zn(II)]. Reaction of the corresponding 2,3-dioxochlorin with p-toluenesulfonylhydrazine yields the desired…
Efficient Silver-Mediated Acetalationof β,β′-Functionalized Chlorins
We present a novel synthetic strategy to 2,2-dialkoxy-3-oxochlorins [M = 2H, Ni(II), Cu(II)] (i.e., acetaloxochlorins). Reaction of the corresponding 2,3-dioxochlorin with stoichiometric amounts of…
Bio-based natural rubber composition and its use
The invention relates to a pressure-sensitive adhesive that is biobased at least 95 wt .-%, preferably 98 wt .-%, containing as the base polymer, natural rubber and tackifier resins from bio-based…