Alkylation of enolate anions formation of enol ethers

G.J. Heiszwolf, H. Kloosterziel

Research output: Contribution to journalArticleAcademicpeer-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 languageEnglish
Pages (from-to)1153-1169
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume89
Issue number11
DOIs
Publication statusPublished - 1970

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Ethers
Alkylation
Anions
Alkylating Agents
Ketones
Aldehydes
Sulfates
Substrates

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Heiszwolf, G.J. ; Kloosterziel, H. / Alkylation of enolate anions formation of enol ethers. In: Recueil des Travaux Chimiques des Pays-Bas. 1970 ; Vol. 89, No. 11. pp. 1153-1169.
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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)]",
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Alkylation of enolate anions formation of enol ethers. / Heiszwolf, G.J.; Kloosterziel, H.

In: Recueil des Travaux Chimiques des Pays-Bas, Vol. 89, No. 11, 1970, p. 1153-1169.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Alkylation of enolate anions formation of enol ethers

AU - Heiszwolf, G.J.

AU - Kloosterziel, H.

PY - 1970

Y1 - 1970

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

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