Tim Zunker - Porphyrin Synthesis in Surfactant Solution:  Multicomponent Assembly in Micelles

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  Publication Details (including relevant citation   information):

  Bonar-Law, Richard P. The Journal of Organic Chemistry  1996 61 (11) 3623-3634

  Abstract: A synthesis of meso-substituted   porphyrins in anionic sodium dodecyl sulfate micelles has been   developed. Polar, functionalized aromatic aldehydes condense   reversibly with pyrrole in the micellar phase. Oxidation of the   porphyrinogen then provides functionalized porphyrins in yields   of 10−48%. Hydrophobic aldehydes condense irreversibly to give   low yields at practical substrate concentrations. Synthesis in   D2O solution results in per-β-deuterated porphyrins. A two-phase   model is used to rationalize the dependence of porphyrin yield on   reactant and surfactant concentration. Micelles are viewed as   potential wells which promote porphyrinogen assembly by binding   products more tightly than reactants.

  Address (URL): http://dx.doi.org/10.1021/jo9600161