214962-07-9Relevant academic research and scientific papers
A new synthetic approach to porphyrin-α-diones and a -2,3,12,13-tetraone: Building blocks for laterally conjugated porphyrin arrays
Promarak, Vinich,Burn, Paul L.
, p. 14 - 20 (2007/10/03)
We report the first use of the Dess-Martin periodinane (DMP) for the oxidation of an arylamine to an α-dione. The methodology is illustrated by the preparation of free-base and metal chelated porphyrin-α-diones in up to 52% yield by oxidation of 2-aminoporphyrins with the DMP. We also found that DMP could be used to oxidise a 2,3-diaminoporphyrin to a porphyrin-α-dione in good yield with other free-base diaminoporphyrin isomers forming a trans-porphyrintetraone in 20% yield.
A study on the oxidation of 2-hydroxyporphyrins to porphyrin-α-diones
Beavington, Richard,Rees, Philip A.,Burn, Paul L.
, p. 2847 - 2851 (2007/10/03)
Porphyrin-α-diones have been used for the preparation of extended rigidly oriented porphyrin systems. Copper 2, free-base 3, and zinc 4 2-hydroxyporphyrins have been prepared by an improved method and treated with a range of oxidants to form the corresponding porphyrin-α-diones, 5, 6, and 7 in yields of up to 94%. We have found that the free-base 2-hydroxyporphyrin 3 was easily oxidised and usually gave the best yields of porphyrin-α-dione. In this study the most effective general oxidant was determined to be the Dess-Martin periodinane which oxidised all three 2-hydroxyporphyrins to their respective porphyrin-α-diones in good yields.
