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Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium
Dobmeier, Michael, Herrmann, Josef M., Lenoir, Dieter und König, Burkhard
(2012)
Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium.
Beilstein Journal of Organic Chemistry 8, S. 330-336.
Veröffentlichungsdatum dieses Volltextes: 08 Mrz 2012 07:29
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.23539
Zusammenfassung
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 ...
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.
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| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Beilstein Journal of Organic Chemistry | ||||
| Verlag: | BEILSTEIN-INSTITUT | ||||
|---|---|---|---|---|---|
| Ort der Veröffentlichung: | FRANKFURT AM MAIN | ||||
| Band: | 8 | ||||
| Seitenbereich: | S. 330-336 | ||||
| Datum | 2012 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identifikationsnummer |
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| Stichwörter / Keywords | HYPOPHOSPHOROUS ACID; INDUCED DEOXYGENATION; ORGANOTIN COMPOUNDS; ALLYLIC ALCOHOLS; HYDROGEN IODIDE; REDUCING SYSTEM; DERIVATIVES; PHOSPHORUS; PHOSPHITES; SECONDARY; | ||||
| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Ja | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-235396 | ||||
| Dokumenten-ID | 23539 |
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