Dobmeier, Michael and Herrmann, Josef M. and Lenoir, Dieter and Koenig, Burkhard (2012) Reduction of benzylic alcohols and alpha-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 8. pp. 330-336. ISSN 1860-5397,
Full text not available from this repository. (Request a copy)Abstract
The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HYPOPHOSPHOROUS ACID; INDUCED DEOXYGENATION; ORGANOTIN COMPOUNDS; ALLYLIC ALCOHOLS; HYDROGEN IODIDE; REDUCING SYSTEM; DERIVATIVES; PHOSPHORUS; PHOSPHITES; SECONDARY; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 18 May 2020 09:33 |
| Last Modified: | 18 May 2020 09:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/19067 |
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