Hydrogen transfer from isopropyl alcohol to unsaturated aldehydes and ketones in the presence of Al2O3

1972 ◽  
Vol 21 (8) ◽  
pp. 1784-1785 ◽  
Author(s):  
V. Z. Sharf ◽  
L. Kh. Freidlin ◽  
N. K. Vorob'eva
Keyword(s):  
Hydrogen Transfer ◽  
Isopropyl Alcohol ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones

Hydrogen transfer reactions. I. Reduction of carbonyl compounds by alcohols catalyzed by alumina

1969 ◽  
Vol 47 (19) ◽  
pp. 3705-3707 ◽  
Author(s):  
D. V. Ramana ◽  
C. N. Pillai
Keyword(s):  
Vapor Phase ◽  
Carbonyl Compounds ◽  
Hydrogen Transfer ◽  
Isopropyl Alcohol ◽  
Aromatic Aldehydes ◽  
Transfer Reactions ◽  
Secondary Alcohols ◽  
Effective Catalyst ◽  
Phase Reduction ◽  
Aldehydes And Ketones

Alumina containing about 2.2% by weight of Na+ has been found to be an effective catalyst for the vapor phase reduction of carbonyl compounds by alcohols and for the reverse reaction, the oxidation of the alcohols by carbonyl compounds. The reduction of a number of aliphatic and aromatic aldehydes and ketones by isopropyl alcohol and the oxidation of a number of primary and secondary alcohols by ketones like acetone and cyclohexanone are reported.

scholarly journals Theoretical Insight into the Reversal of Chemoselectivity in Diels-Alder Reactions of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Brønsted and Lewis Acids

Organics ◽  
2021 ◽  
Vol 2 (1) ◽  
pp. 38-49
Author(s):  
Lakhdar Benhamed ◽  
Sidi Mohamed Mekelleche ◽  
Wafaa Benchouk
Keyword(s):  
Lewis Acids ◽  
Major Product ◽  
Diels Alder ◽  
Unsaturated Ketone ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones ◽  
Theoretical Insight ◽  
Insight Into ◽  
Good Agreement

Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions of α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones (e.g., 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, the reaction gave a Diels–Alder adduct derived from α,β-unsaturated ketone as a major product. On the other hand, the use of tris(pentafluorophenyl)borane B(C6F5)3 bulky Lewis acid as catalyst gave mainly the cycloadduct of α,β-unsaturated aldehyde as a major product. Our aim in the present work is to put in evidence the role of the catalyst in the reversal of the chemoselectivity of the catalyzed Diels–Alder reactions of (2E)-but-2-enal and 2-Hexen-4-one with cyclopentadiene. The calculations were performed at the ωB97XD/6-311G(d,p) level of theory and the solvent effects of dichloromethane were taken into account using the PCM solvation model. The obtained results are in good agreement with experimental outcomes.

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