Alkylation of enolate anions formation of enol ethers

G.J. Heiszwolf; H. Kloosterziel

doi:10.1002/recl.19700891106

Alkylation of enolate anions formation of enol ethers

G.J. Heiszwolf, H. Kloosterziel

Department of Chemical Engineering and Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

36 Citations (Scopus)

Abstract

The alkylation of ambident enolate anions-obtained from aliphatic ketones (and one particular type of aldehyde)-was studied using various solvents, bases, alkylating agents and substrates. Alkylation with a reactive alkylating agent (dialkyl sulfates, triethyloxonium fluoroborate) in an aprotic polar solvent (e.g., Me2SO) yields mainly enol ethers, the products of alkylation at O. The predominance of alkylation at O over alkylation at C in these fast reactions and the behavior of the various enolate anions are interpreted with the aid of the principle of least motion. [on SciFinder (R)]

Original language	English
Pages (from-to)	1153-1169
Journal	Recueil des Travaux Chimiques des Pays-Bas
Volume	89
Issue number	11
DOIs	https://doi.org/10.1002/recl.19700891106
Publication status	Published - 1970

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Heiszwolf, G. J., & Kloosterziel, H. (1970). Alkylation of enolate anions formation of enol ethers. Recueil des Travaux Chimiques des Pays-Bas, 89(11), 1153-1169. https://doi.org/10.1002/recl.19700891106

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abstract = "The alkylation of ambident enolate anions-obtained from aliphatic ketones (and one particular type of aldehyde)-was studied using various solvents, bases, alkylating agents and substrates. Alkylation with a reactive alkylating agent (dialkyl sulfates, triethyloxonium fluoroborate) in an aprotic polar solvent (e.g., Me2SO) yields mainly enol ethers, the products of alkylation at O. The predominance of alkylation at O over alkylation at C in these fast reactions and the behavior of the various enolate anions are interpreted with the aid of the principle of least motion. [on SciFinder (R)]",

author = "G.J. Heiszwolf and H. Kloosterziel",

year = "1970",

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T1 - Alkylation of enolate anions formation of enol ethers

AU - Heiszwolf, G.J.

AU - Kloosterziel, H.

PY - 1970

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N2 - The alkylation of ambident enolate anions-obtained from aliphatic ketones (and one particular type of aldehyde)-was studied using various solvents, bases, alkylating agents and substrates. Alkylation with a reactive alkylating agent (dialkyl sulfates, triethyloxonium fluoroborate) in an aprotic polar solvent (e.g., Me2SO) yields mainly enol ethers, the products of alkylation at O. The predominance of alkylation at O over alkylation at C in these fast reactions and the behavior of the various enolate anions are interpreted with the aid of the principle of least motion. [on SciFinder (R)]

AB - The alkylation of ambident enolate anions-obtained from aliphatic ketones (and one particular type of aldehyde)-was studied using various solvents, bases, alkylating agents and substrates. Alkylation with a reactive alkylating agent (dialkyl sulfates, triethyloxonium fluoroborate) in an aprotic polar solvent (e.g., Me2SO) yields mainly enol ethers, the products of alkylation at O. The predominance of alkylation at O over alkylation at C in these fast reactions and the behavior of the various enolate anions are interpreted with the aid of the principle of least motion. [on SciFinder (R)]

U2 - 10.1002/recl.19700891106

DO - 10.1002/recl.19700891106

M3 - Article

VL - 89

SP - 1153

EP - 1169

JO - Recueil des Travaux Chimiques des Pays-Bas

JF - Recueil des Travaux Chimiques des Pays-Bas

SN - 0165-0513

IS - 11

ER -

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10.1002/recl.19700891106