Energetic and rate effects of the trifluoromethyl group at C-2 and C-4 on the aliphatic Claisen rearrangement

1990 ◽  
Vol 55 (6) ◽  
pp. 1813-1822 ◽  
Author(s):  
Joseph J. Gajewski ◽  
Kyle R. Gee ◽  
J. Jurayj
Keyword(s):  
Claisen Rearrangement ◽  
Trifluoromethyl Group ◽  
Rate Effects

Gosteli−Claisen Rearrangement: DFT Study of Substituent−Rate Effects

2009 ◽  
Vol 74 (11) ◽  
pp. 4336-4342 ◽  
Author(s):  
Julia Rehbein ◽  
Martin Hiersemann
Keyword(s):  
Claisen Rearrangement ◽  
Dft Study ◽  
Rate Effects

Highly diastereo- and enantioselective organocatalytic synthesis of trifluoromethylated erythritols based on the in situ generation of unstable trifluoroacetaldehyde

2021 ◽  
Author(s):  
Kazumasa Funabiki ◽  
Toshiya Gotoh ◽  
Ryunosuke Kani ◽  
Toshiyasu Inuzuka ◽  
Yasuhiro Kubota
Keyword(s):  
Trifluoromethyl Group ◽  
In Situ Generation

A highly diastereo- and enantioselective organocatalytic method to synthesise erythritols bearing a trifluoromethyl group has been investigated.

The reinforcing and rate effects of intracranial dopamine administration.

1986 ◽  
Author(s):  
Steven I. Dworkin ◽  
Nick E. Goeders ◽  
James E. Smith
Keyword(s):  
Rate Effects

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.

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