Abstract
Oxidation of alcohols to the corresponding carbonyl compounds using triacetoxyperiodinane. The Dess–Martin periodinane, 1,1,1-triacetoxy-1,1- dihydro-1,2-benziodoxol-3(1H)-one, is one of the most useful oxidant for the conversion of primary and secondary alcohols to their corresponding aldehyde or ketone products, respectively.
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(a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155–4156. James Cullen (J. C.) Martin (1928–1999) had a distinguished career spanning 36 years both at the University of Illinois at Urbana-Champaign and Vanderbilt University. J. C.’s formal training in physical organic chemistry with Don Pearson at Vanderbilt and P. D. Bartlett at Harvard prepared him well for his early studies on carbocations and radicals. However, it was his interest in understanding the limits of chemical bonding that led to his landmark investigations into hypervalent compounds of the main group elements. Over a 20-year period the Martin laboratories successfully prepared unprecedented chemical structures from sulfur, phosphorus, silicon and bromine while the ultimate “Holy Grail” of stable pentacoordinate carbon remained elusive. Although most of these studies were driven by J. C.’s fascination with unusual bonding schemes, they were not without practical value. Two hypervalent compounds, Martin’s sulfurane (for dehydration) and the Dess–Martin periodinane have found widespread application in synthetic organic chemistry. J. C. Martin and his student Daniel Dess developed this methodology at the University of Illinois at Urbana. (Martin’s biography was kindly supplied by Prof. Scott E. Denmark). (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277–7287.
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Li, J.J. (2014). Dess–Martin periodinane oxidation. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_86
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DOI: https://doi.org/10.1007/978-3-319-03979-4_86
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