Labinger, Jay A. and Herring, Andrew M. and Bercaw, John E. (1992) Selective Hydroxylation of Hydrocarbons by Platinum Salts in Aqueous Media Direct Conversion of Ethanol to Ethylene Glycol. In: Homogeneous Transition Metal Catalyzed Reactions. ACS Symposium Series. No.230. American Chemical Society , Washington, DC, pp. 221-232. ISBN 9780841220072. https://resolver.caltech.edu/CaltechAUTHORS:20180405-131938956
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Abstract
Water-soluble organic compounds are hydroxylated by aqueous solutions of chloroplatinum(II) and chloroplatinum(IV) salts. p-Toluenesulfonic acid is converted stepwise to the corresponding alcohol and aldehyde, the first step being somewhat faster than the second. No further conversion to the carboxylic acid is observed. Ethanol shows substantial selectivity for attack at a C-H bond of the methyl group, affording ethylene glycol and 2-chloroethanol, as well as more expected products such as acetaldehyde and acetic acid. The origin of the unusual selectivity patterns is discussed in terms of the mechanism of activation of C-H bonds by Pt(II) species.
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| Additional Information: | © 1992 American Chemical Society. Received for review October 19, 1990. Accepted revised manuscript September 24, 1991. Published in print 1 March 1992. This research was supported by the Caltech Consortium in Chemistry and Chemical Engineering (founding members: Ε. I. du Pont de Nemours and Company, Inc., Eastman Kodak Company, Minnesota Mining and Manufacturing Company, and Shell Development Company) and by the Office of Naval Research, Grant N00014-89-J-3198. A. M. Herring thanks the Science and Engineering Research Council (United Kingdom) for a NATO fellowship. | ||||||||||||||||
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| Series Name: | ACS Symposium Series | ||||||||||||||||
| Issue or Number: | 230 | ||||||||||||||||
| DOI: | 10.1021/ba-1992-0230.ch015 | ||||||||||||||||
| Record Number: | CaltechAUTHORS:20180405-131938956 | ||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20180405-131938956 | ||||||||||||||||
| Official Citation: | Selective Hydroxylation of Hydrocarbons by Platinum Salts in Aqueous Media Jay A. Labinger, Andrew M. Herring, and John E. Bercaw Homogeneous Transition Metal Catalyzed Reactions. March 1, 1992, 221-232 DOI:10.1021/ba-1992-0230.ch015 | ||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||
| ID Code: | 85644 | ||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||||||||
| Deposited On: | 05 Apr 2018 20:49 | ||||||||||||||||
| Last Modified: | 15 Nov 2021 20:30 |
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