Methyl Deuteration Reactions in Vinylporphyrins: Protoporphyrins IX, III, and XIII
Base-catalyzed deuteration of the methyl groups in protoporphyrin IX dimethyl ester (1) proceeds with differential deuteration; rate of deuteration, as measured by NMR spectroscopy of reaction products, follows the order 3-Me > 1-Me > 5-Me > 8-Me. A simple qualitative theory to explain the differential deuteration is discussed, based on primary (vinyl group on subunit bearing the deuteriated methyl) and secondary (vinyl group on adjacent subunits) inductive effects, and this is tested by using the symmetrical porphyrins, protoporphyrin III dimethyl ester (6) and protoporphyrin XIII dimethyl ester (7). Synthesis of 6 and 7, from monopyrroles via the a,c-biladiene route, are reported. © 1986, American Chemical Society. All rights reserved.
Publication Source (Journal or Book title)
Journal of Organic Chemistry
Smith, K., Parish, D., & Inouye, W. (1986). Methyl Deuteration Reactions in Vinylporphyrins: Protoporphyrins IX, III, and XIII. Journal of Organic Chemistry, 51 (5), 666-671. https://doi.org/10.1021/jo00355a016