CHEMICAL REVIEWS VOLUME 67,
NUMBER3
MAY25, 1967
DIMETHYL SULFOXIDE OXIDATIONS W. W. EPSTEIN AND F. W. SWEAT Department of Chemistry, University of Utah, Salt Lake City, Utah Received July 13, 1966 CONTENTS
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A. Toxicity. .....
11. General Considerations.. ................................. A. DMSO. Structure and Reactivity. . . . . . . . . . . . .
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111. DMSO DCC Method. . . A. General.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . B. The Oxidation of Nucleotides and Nucleosides. . . . . . . . . ........... C. Oxidation of Carbohydrates. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . IV. Acetic Anhydride Method. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . V. Phosphorus Pentoxide Method. . . .................. VI. Chloroformate Method. . . . . . . VII. Oxidation of Halides and Tosylates VIII. Oxidation of Thiols. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . I X . Miscellaneous Oxidations. . . . . ........ A. Diazonium Method.. . . . . B. Oxidation of Sulfides.. ....................... C. Oxidation of Ketenes and Related Compounds. . D. Air Oxidation of Alcohols. E. Oxidation of Inorganic Halides.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . F. Oxidation of Quinol Acetates. . . . . G. Oxidative Halogenation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . H. Oxidation of Epoxides. . . . . . . X. References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
I. INTRODUCTION
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compounds in dimethyl sulfoxide are potentially danger-
compounds (17a)*
first employed as an oxidizing agent
