Medium basicity effects on the transition state structure of E2 reactions. Kinetic study of the reaction of 1-chloro-1-phenyl-2-arylethanes with crown ether complexed potassium tert-butoxide in tert-butyl alcohol

1977 ◽  
Vol 42 (12) ◽  
pp. 2170-2172 ◽  
Author(s):  
Sergio Alunni ◽  
Enrico Baciocchi ◽  
Piero Perucci
Keyword(s):  
Crown Ether ◽  
Transition State ◽  
Kinetic Study ◽  
Butyl Alcohol ◽  
State Structure ◽  
Transition State Structure ◽  
Tert Butyl ◽  
Tert Butyl Alcohol

Using secondary alpha deuterium kinetic isotope effects to determine the stereochemistry of an E2 reaction; the stereochemistry of the E2 reaction of 1-chloro-2-phenylethane with potassium tert-butoxide in tert-butyl alcohol

2001 ◽  
Vol 79 (7) ◽  
pp. 1145-1152 ◽  
Author(s):  
Peter James Smith ◽  
David AJ Crowe ◽  
Kenneth Charles Westaway
Keyword(s):  
Transition State ◽  
Isotope Effects ◽  
Kinetic Isotope Effects ◽  
Butyl Alcohol ◽  
State Structure ◽  
Transition State Structure ◽  
Isotopic Labelling ◽  
Tert Butyl ◽  
Kinetic Isotope ◽  
Tert Butyl Alcohol

Isotopic labelling studies have shown that the E2 reaction of 1-chloro-2-phenylethane with potassium tert-butoxide in tert-butyl alcohol occurs via an anti-periplanar stereochemistry. This demonstrates that the different secondary alpha deuterium kinetic isotope effects found for the high and low base concentrations and in the presence of 18-crown-6 ether are because of changes in transition state structure that occur when the form of the reacting base changes rather than to a change in the stereochemistry of the reaction.Key words: E2 reaction, stereochemistry, secondary alpha deuterium kinetic isotope effects, transition state.

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