Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates
- Award ID(s):
- 1700982
- PAR ID:
- 10172597
- Date Published:
- Journal Name:
- Journal of the American Chemical Society
- Volume:
- 139
- Issue:
- 43
- ISSN:
- 0002-7863
- Page Range / eLocation ID:
- 15539 to 15547
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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Carbaporphyrins exhibit rich and unique reactivities that form stable organometallic derivatives and unique oxidation reactions. In this review, the regioselective oxidation of carbaporphyrinoids is surveyed. True carbaporphyrins undergo core oxidation to give aromatic carbaporphyrin ketals and weakly aromatic oxycarbaporphyrins, while carbaporphyrin carbaldehydes are converted into aromatic trioxycarbaporphyrins. Azuliporphyrins are easily oxidized to benzocarbaporphyrins and nonaromatic 21-oxyazuliporphyrins. Oxidative metalations are also commonly observed in this system. In addition, other carbaporphyrinoids, including N-confused porphyrins and benziporphyrins, give rise to remarkable oxidation reactions that afford intriguing new structures.more » « less
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