scholarly journals Kinetics of the reactions of laser-flash photolytically generated carbenium ions with alkyl and silyl enol ethers. Comparison with the reactivity toward alkenes, allylsilanes and alcohols

1991 ◽  
Vol 113 (20) ◽  
pp. 7710-7716 ◽  
Author(s):  
Joerg Bartl ◽  
Steen Steenken ◽  
Herbert Mayr
Keyword(s):  
Laser Flash ◽  
Enol Ethers ◽  
Carbenium Ions ◽  
Silyl Enol Ethers ◽  
Kinetics Of

scholarly journals Metal Enolates – Enamines – Enol Ethers: How Do Enolate Equivalents Differ in Nucleophilic Reactivity?

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1157-1170 ◽  
Author(s):  
Artem Leonov ◽  
Daria Timofeeva ◽  
Armin Ofial ◽  
Herbert Mayr
Keyword(s):  
Rate Constants ◽  
Correlation Equation ◽  
Stopped Flow ◽  
Quinone Methides ◽  
Enol Ethers ◽  
Reactivity Descriptors ◽  
Silyl Enol Ethers ◽  
Nucleophilic Reactivity ◽  
Kinetics Of ◽  
Least Squares Minimization

The kinetics of the reactions of trimethylsilyl enol ethers and enamines (derived from deoxybenzoin, indane-1-one, and α-tetralone) with reference electrophiles (p-quinone methides, benzhydrylium and indolylbenzylium ions) were measured by conventional and stopped-flow photometry in acetonitrile at 20 °C. The resulting second-order rate constants were subjected to a least-squares minimization based on the correlation equation lg k = s N(N + E) for determining the reactivity descriptors N and s N of the silyl enol ethers and enamines. The relative reactivities of structurally analogous silyl enol ethers, enamines, and enolate anions towards carbon-centered electrophiles are determined as 1, 107, and 1014, respectively. A survey of synthetic applications of enolate ions and their synthetic equivalents shows that their behavior can be properly described by their nucleophilicity parameters, which therefore can be used for designing novel synthetic transformations.

Addition of Allylsilanes and Silyl Enol Ethers to Small Oxygenated Rings: New Tools for Organic Synthesis

2014 ◽  
Vol 18 (5) ◽  
pp. 525-546 ◽  
Author(s):  
Carmen Hernandez-Cervantes ◽  
Miriam Alvarez-Corral ◽  
Manuel Munoz-Dorado ◽  
Ignacio Rodriguez-Garcia
Keyword(s):  
Organic Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

Bench‐Stable Electrophilic Fluorinating Reagents for Highly Selective Mono‐ and Difluorination of Silyl Enol Ethers

2021 ◽  
Author(s):  
Kohsuke Aikawa ◽  
KyoKo Nozaki ◽  
Takashi Okazoe ◽  
Yuichiro Ishibashi ◽  
Akiya Adachi
Keyword(s):  
Enol Ethers ◽  
Silyl Enol Ethers

ChemInform Abstract: Lewis-Acid-Induced Reactions of α-Methoxyglycinamide Derivatives with Silyl Enol Ethers. Formation of 3-Amino-2-pyrrolidinones and 3- Amino-2-pyrrolinones.

ChemInform ◽  
2010 ◽  
Vol 23 (48) ◽  
pp. no-no
Author(s):  
E. C. ROOS ◽  
H. HIEMSTRA ◽  
W. N. SPECKAMP ◽  
B. KAPTEIN ◽  
J. KAMPHUIS ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Enol Ethers ◽  
Silyl Enol Ethers

ChemInform Abstract: Allylation and Benzylation of Enolates Derived from β- Phenylselanyl Silyl Enol Ethers.

ChemInform ◽  
2010 ◽  
Vol 28 (38) ◽  
pp. no-no
Author(s):  
S. PONTHIEUX ◽  
F. OUTURQUIN ◽  
C. PAULMIER
Keyword(s):  
Enol Ethers ◽  
Silyl Enol Ethers
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