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Why is alkylation of an enolate accompanied by so much polyalkylation?
A Streitwieser1, Y J Kim, D Z Wang
1Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA. astreit@socrates.berkeley.edu
Organic Letters
|August 3, 2001
Abstract:
[reaction: see text] The lithium enolate 1-Li of 6-phenyl-alpha-tetralone forms a monomer-tetramer equilibrium in THF at 25 degrees C with K(1,4) = 4.7E+10 M(-3). The lithium enolate 2-Li, however, forms a monomer-dimer equilibrium with K(1,2) = 3800 M(-1). In both cases reaction with benzyl bromide is dominantly with the monomer. The results support an earlier conjecture of House that alkylation of an enolate is frequently accompanied by extensive polyalkylation because the less substituted enolates are more aggregated.