Effect of M eso-Substituents on the Osmium Tetraoxide Reaction and Pinacol-Pinacolone Rearrangement of the Corresponding v ic-Dihydroxyporphyrins

Y Chen, CJ Medforth, KM Smith, J Alderfer…

Index: Chen; Medforth; Smith; Alderfer; Dougherty; Pandey Journal of Organic Chemistry, 2001 , vol. 66, # 11 p. 3930 - 3939

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Citation Number: 25

Abstract

To investigate the effects of electron-donating and electron-withdrawing substituents upon the reaction of porphyrins with osmium tetraoxide, and the pinacol-pinacolone rearrangement of the resulting diols, a series of meso-substituted porphyrins were prepared by total synthesis. Porphyrins with electron-donating substitutents at the meso-positions gave vic-dihydroxychlorins in which the adjacent pyrrole subunit was predominantly ...