ChemInform Abstract: Dienediolates of Unsaturated Carboxylic Acids in Synthesis. Aldehydes and Ketones from Alkyl Halides, by Ozonolysis of β,γ- Unsaturated α-Alkyl Carboxylic Acids. The Role of a Tertiary Amine in the Cleavage of Ozonides.

ChemInform ◽  
2010 ◽  
Vol 28 (51) ◽  
pp. no-no
Author(s):  
M. J. AURELL ◽  
L. CEITA ◽  
R. MESTRES ◽  
A. TORTAJADA
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Alkyl Halides ◽  
Aldehydes And Ketones ◽  
Unsaturated Carboxylic Acids

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

Perturbation theory of substituent effect. Importance of the field effect in transmission of the substituent effect

1980 ◽  
Vol 45 (6) ◽  
pp. 1655-1661 ◽  
Author(s):  
Robert Ponec
Keyword(s):  
Perturbation Theory ◽  
Carboxylic Acids ◽  
Quantum Chemical ◽  
Substituent Effect ◽  
Field Effect ◽  
Adequate Description ◽  
Meta Position ◽  
Unsaturated Carboxylic Acids

Various quantum chemical approaches to the problem of transmission of the substituent effect were compared. It was shown that inclusion of the electronic repulsion (field effect) was necessary to give a true picture of differences in ρ constants for reactions of the cis and trans isomers of substituted unsaturated carboxylic acids; the same holds for an adequate description of transmission of the substituent effect from the meta position on a given skeleton.

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.

scholarly journals Copper(I) Chloride/Kieselguhr: A Versatile Catalyst for Oxidation of Alkyl Halides and Alkyl Tosylates to the Carbonyl Compounds

1999 ◽  
Vol 23 (7) ◽  
pp. 434-435
Author(s):  
Mohammed M. Hashemi ◽  
Yousef Ahmadi Beni
Keyword(s):  
Carbonyl Compounds ◽  
Alkyl Halides ◽  
Aldehydes And Ketones ◽  
High Yields

Copper(I) Chloride adsorbed on Kieselguhr in the presence of oxygen catalyses oxidation of alkyl halides and alkyl tosylates to the aldehydes and ketones in high yields.

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