Additions and Corrections: The Mechanism of the Acid-catalyzed Aromatic Hydrogen Exchange.

1959 ◽  
Vol 81 (24) ◽  
pp. 6537-6537
Author(s):  
A Kresge ◽  
Y Chiang
Keyword(s):  
Hydrogen Exchange ◽  
Acid Catalyzed ◽  
Aromatic Hydrogen

Hydrogen exchange and isomerization in ortho substituted benzamides. On the question of free rotation in an N-protonated amide

1979 ◽  
Vol 57 (22) ◽  
pp. 2896-2901 ◽  
Author(s):  
Robert A. McClelland ◽  
William F. Reynolds
Keyword(s):  
Exchange Reaction ◽  
Rate Constants ◽  
Hydrogen Exchange ◽  
Isomerization Reaction ◽  
Free Rotation ◽  
Bond Rotation ◽  
Diffusion Limited ◽  
Deprotonation Reaction ◽  
Substituted Benzamides ◽  
Acid Catalyzed

Rate constants have been obtained for the acid-catalyzed N–H exchange of N-methyl, 2,N-dimethyl, and 2,4,6,N-tetramethylbenzamide and the acid-catalyzed isomerization of the three corresponding N,N-dimethylbenzamides. The ratio [Formula: see text] increases significantly with increased number of ortho methyl substituents. This is explained in terms of a suggestion of Perrin, that C—N bond rotation is not completely free in the N-protonated amide, since it must compete with a diffusion limited deprotonation reaction. The isomerization reaction, which requires such a rotation, is therefore slowed by ortho methyl substituents which hinder rotation, relative to the exchange reaction, which does not require rotation.

Clay catalysis of aromatic hydrogen-exchange reactions

1982 ◽  
Vol 46 (2) ◽  
pp. 219-222 ◽  
Author(s):  
Robert Alexander ◽  
Robert Ian Kagi ◽  
Alfons Valentino Larcher
Keyword(s):  
Hydrogen Exchange ◽  
Exchange Reactions ◽  
Clay Catalysis ◽  
Aromatic Hydrogen

scholarly journals The Silicon–Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

Synlett ◽  
2021 ◽  
Author(s):  
Benjamin List ◽  
Hui Zhou ◽  
Pinglu Zhang
Keyword(s):  
Exchange Reaction ◽  
Hydrogen Exchange ◽  
Kinetic Resolution ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Cyclic Ketones ◽  
Silicon Source ◽  
Acid Catalyzed

We have recently reported the strong and confined, chiral acid-catalyzed asymmetric “silicon−hydrogen exchange reaction”. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.

Aromatic protonation. VI. Broensted relation for aromatic hydrogen exchange in 1,3,5-trimethoxybenzene

1970 ◽  
Vol 92 (21) ◽  
pp. 6309-6314 ◽  
Author(s):  
A. Jerry. Kresge ◽  
Sanford. Slae ◽  
David W. Taylor
Keyword(s):  
Hydrogen Exchange ◽  
Aromatic Hydrogen
Sign in / Sign up

Export Citation Format

Share Document