A combination of aluminium and nickel chloride in THF has been shown to effect the selective reduction of the olefinic double bond of the d-enone system. Isolated double bonds and aliphatic carbonyls remain unaffected under these conditions. However, aromatic aldehydes and ketones are converted to t
Selective, C,C-double bond reduction of α,β-unsaturated carbonyl compounds with cyclohexane using zeolites
✍ Scribed by Konstantin Yu. Koltunov; Stéphane Walspurger; Jean Sommer
- Publisher
- Elsevier Science
- Year
- 2006
- Tongue
- English
- Weight
- 134 KB
- Volume
- 245
- Category
- Article
- ISSN
- 1381-1169
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✦ Synopsis
Selective ionic hydrogenation of ␣,-unsaturated carbonyl compounds with alkanes (cyclohexane and others) was previously known to proceed only in superacidic conditions due to the necessity of dicationic, superelectrophilic activation of the enones. In present paper we disclose that H-form zeolites with acidity well below superacidity, are able however to induce the reduction of ␣,-unsaturated carbonyl compounds with cyclohexane in strong analogy to the "parent", superacid mediated reactions. The probable interpretation of these results in terms of highly electrophilic (superelectrophilic) intermediates on the solid is discussed.
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