ChemInform Abstract: SECONDARY DEUTERIUM ISOTOPE EFFECT IN AN ELECTROPHILIC AROMATIC SUBSTITUTION - PROTODESILYLATION OF TRIMETHYLPHENYLSILANE

1982 ◽  
Vol 13 (14) ◽  
Author(s):  
I. SZELE
Keyword(s):  
Isotope Effect ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Deuterium Isotope Effect

AROMATIC SUBSTITUTION: PART V. THE MECHANISM OF THE REACTION OF PHENYLLITHIUM WITH PYRIDINES. DEUTERIUM ISOTOPE EFFECT STUDIES

1963 ◽  
Vol 41 (12) ◽  
pp. 3127-3131 ◽  
Author(s):  
R. A. Abramovitch ◽  
Choo-Seng Giam
Keyword(s):  
Isotope Effect ◽  
Experimental Error ◽  
Aromatic Substitution ◽  
Deuterium Isotope Effect ◽  
Hydride Ion ◽  
Nucleophilic Aromatic Substitutions ◽  
Mechanism Of The Reaction

The ratios of isomers formed in the reaction of 3-alkylpyridines with phenyllithium under various conditions appear to be invariant within the limits of experimental error. A number of experiments, including the reaction of phenyllithium with 3-picoline-2d and with an excess of a mixture of pyridine and pyridine-2d, are described which establish that the hydride ion elimination stage in these nucleophilic aromatic substitutions is not important in determining the observed orientation and that the addition stage is either virtually irreversible or that the equilibrium lies far on the product side and is not rapidly reversible. A convenient new procedure is described for working up the reaction mixtures.

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