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by: Michelle Gulgowski DVM


Marketplace > University of Kentucky > Chemistry > CHE 535 > SYNTHETIC ORGANIC CHEM
Michelle Gulgowski DVM
GPA 3.91


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Class Notes
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This 2 page Class Notes was uploaded by Michelle Gulgowski DVM on Friday October 23, 2015. The Class Notes belongs to CHE 535 at University of Kentucky taught by Staff in Fall. Since its upload, it has received 22 views. For similar materials see /class/228301/che-535-university-of-kentucky in Chemistry at University of Kentucky.




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Date Created: 10/23/15
Chem 535 Synthetic Organic Chemistry Common Oxidizing Agents for the Conversion of ROH Functionality Name Composition Typical Use Scope amp Limitations Jones Reagent most HzCrzO7 OH O The chromium reactive of the reagent oxidizes common Chromium 0r NaZCrZO7 H2304 R R amines sul des based oxidizing Cleaves 12diaols reagents1 OH and related d q functionaliy o RCHzOH gt RCOzH Collins Reagentz393 Cr03 NC5H5CH2C12 0 Large excess often needed messy Cr03 Pyz o workup PCCpyridinium PyHClCr03 same as collins Method of choice chlorochromate4 Reagent is a solid 15 equivs excess usually suffices can buffer acidic reagent with NaOAc PDC5 2Py CrzO7 RCHzOH gt RCOzH probably better than jones Active MnOz6 I OH Benzyl allyl cyclopropylcarbinyl alcohols are selectively oxidized Swem7 DMSO Oxalyl l0 or 20 alcohol to won t oxidize RzS or chloride NEt3 aldehyde or ketone NR3 or cleave diols or Vsubheteroatom carbonyls Moffatts DMSO RNCNR as in Swem Hor DMSO AczO NaClOz 9 aqueous systems RCHO D RCOzH Method of Choice in complex systems DessMartin reagent10 AGO A RCHzOHD RCHO Very mild conditions c o A c RR CHOHDRCOR o o H o References l K B Wiberg Oxidation in Organic Chemistry Academic Press 1965 Ch 2 later volumes in the series 2 Ratcliffe and Rodehorst J Org Chem 1970 35 4000 3 Dauben et al J Org Chem 1978 43 2056 4 a Review Piancatelli Synthesis 1982 245 b Dauben et al J Org Chem 1977 42 682 5 E J Corey et al Tetrahedron Lett 1979 399 6 Carpino et al J Org Chem 1970 35 3971 7 D Swem J Org Chem 1979 44 4148 8 Review Mancuso and Swem Synthesis 1981 165 9 a V P Kudesia Bull Soc Chim Belg 1972 81 623 b Dalcenale E Montanari F J Org Chem 1986 51 567 10 DB Dess JC Martin J Org Chem 1983 48 4155


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