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Alkylation of enolates: An electrophilicity perspective
Author(s) -
Elango M.,
Parthasarathi R.,
Subramanian V.,
Chattaraj P. K.
Publication year - 2005
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20844
Subject(s) - alkylation , chemistry , electrophile , nucleophile , reactivity (psychology) , regioselectivity , lithium (medication) , solvent , organic chemistry , computational chemistry , catalysis , medicine , alternative medicine , pathology , endocrinology
Abstract Enolates are ambient nucleophiles, and alkylation can occur either at a carbon or at an oxygen site. It is known that the ratio of C/O alkylation depends significantly on various factors, including the type of enolate, alkylating agent, site of alkylation, and solvent environment. Analysis of regioselectivity and solvent effects on alkylation of lithium enolates is investigated using various reactivity descriptors, including generalized philicity. These results point out the reliability of both global and local reactivity descriptors in providing significant information about site selectivity and chemical reactivity of lithium enolates. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem, 2006