Electrophilic substitution at saturated carbon. XXXVI. Correlations between rates of potassium methoxide catalyzed hydrogen-deuterium exchange reactions of carbon acids and H

1968 ◽  
Vol 90 (7) ◽  
pp. 1784-1791 ◽  
Author(s):  
Willy D. Kollmeyer ◽  
Donald J. Cram
Keyword(s):  
Electrophilic Substitution ◽  
Deuterium Exchange ◽  
Hydrogen Deuterium Exchange ◽  
Exchange Reactions ◽  
Potassium Methoxide ◽  
Hydrogen Deuterium ◽  
Carbon Acids

Hydrogen-deuterium-exchange reactions of methoxide-methanol clusters

1990 ◽  
Vol 112 (19) ◽  
pp. 6832-6838 ◽  
Author(s):  
S. E. Barlow ◽  
Dang Thuy Thanh ◽  
Veronica M. Bierbaum
Keyword(s):  
Deuterium Exchange ◽  
Hydrogen Deuterium Exchange ◽  
Exchange Reactions ◽  
Hydrogen Deuterium

Hydrogen-deuterium exchange reactions of carbanions with deuterated alcohols in the gas phase

1978 ◽  
Vol 100 (9) ◽  
pp. 2921-2922 ◽  
Author(s):  
C. H. DePuy ◽  
Veronica M. Bierbaum ◽  
Gary K. King ◽  
R. H. Shapiro
Keyword(s):  
Gas Phase ◽  
Deuterium Exchange ◽  
Hydrogen Deuterium Exchange ◽  
Exchange Reactions ◽  
Hydrogen Deuterium

2,4-Diazapentadienes. II. A Carbanion Cyclization

1972 ◽  
Vol 50 (5) ◽  
pp. 678-689 ◽  
Author(s):  
D. H. Hunter ◽  
S. K. Sim
Keyword(s):  
Isotope Effect ◽  
Solvent Effects ◽  
Isotope Effects ◽  
Substituent Effects ◽  
Deuterium Exchange ◽  
Hydrogen Deuterium Exchange ◽  
Deuterium Isotope Effect ◽  
Potassium Methoxide ◽  
Proton Shift ◽  
Hydrogen Deuterium

The mechanism of the cyclization and 1,3-proton shift of 1,3,5-triaryl-2,4-diaza-1,3-pentadienes (1) catalyzed by phenyllithium and by potassium methoxide–methanol has been studied. On the basis of substituent effects, hydrogen–deuterium exchange, isotope effects, and solvent effects, it was deduced that both the cyclization and prototropy involve a common W-shaped carbanion which rapidly cyclizes. A kinetic deuterium isotope effect of 2 was calculated for protonation of this intermediate carbanion in methanol.

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