Alkylation of Ketene Silyl Acetals with Nitroolefins Mediated by Sterically Encumbered Lewis Acids

1997 ◽  
Vol 62 (13) ◽  
pp. 4370-4375 ◽  
Author(s):  
John A. Tucker ◽  
Terrance L. Clayton ◽  
Donald M. Mordas
Keyword(s):  
Lewis Acids ◽  
Silyl Acetals

ChemInform Abstract: Alkylation of Ketene Silyl Acetals with Nitroolefins Mediated by Sterically Encumbered Lewis Acids.

ChemInform ◽  
2010 ◽  
Vol 28 (48) ◽  
pp. no-no
Author(s):  
J. A. TUCKER ◽  
T. L. CLAYTON ◽  
D. M. MORDAS
Keyword(s):  
Lewis Acids ◽  
Silyl Acetals

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 Understanding How Lewis Acids Dope Organic Semiconductors: A “Complex” Story

2021 ◽  
Author(s):  
Pablo Simon Marques ◽  
Giacomo Londi ◽  
Brett Yurash ◽  
Thuc-Quyen Nguyen ◽  
Stephen Barlow ◽  
...  
Keyword(s):  
Organic Semiconductors ◽  
Lewis Acids ◽  
Computational Studies

We report on computational studies of the potential of three borane Lewis acids (LAs) (B(C6F5)3 (BCF), BF3, and BBr3) to form stable adducts and/or to generate positive polarons with three...

scholarly journals Bulky Polyfluorinated Terphenyldiphenylboranes. Water Tolerant Lewis Acids

2020 ◽  
Author(s):  
Corina Stoian ◽  
Marian Olaru ◽  
Theodor Cucuiet ◽  
Krisztina Kegyes ◽  
Alexandru Sava ◽  
...  
Keyword(s):  
Lewis Acids
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