| Literature DB >> 11483070 |
A Streitwieser1, Y J Kim, D Z Wang.
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.Entities:
Year: 2001 PMID: 11483070 DOI: 10.1021/ol0162872
Source DB: PubMed Journal: Org Lett ISSN: 1523-7052 Impact factor: 6.005