Silyl- and germylmercurials in organic synthesis. A new route to O-silylated and O-germylated enolates

O. A. Kruglaya; L. I. Belousova; D. V. Gendin; I. D. Kalikhman; N. S. Vyazankin

doi:10.1016/S0022-328X(00)92565-8

Silyl- and germylmercurials in organic synthesis. A new route to O-silylated and O-germylated enolates

O. A. Kruglaya, L. I. Belousova, D. V. Gendin, I. D. Kalikhman, N. S. Vyazankin

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Abstract

The exchange reaction of α-mercurated ketones with bis(triethylsilyl)- (I) and bis(triethylgermyl)mercury (II) leads to the formation of the corresponding triethylsilyl and triethylgermyl enol ethers. O-Silylated and O-germylated enolates derived from ketones and aldehydes can be also prepared by treating mercurials I and II with appropriate α-bromo-carbonyl compounds. This new pathway also represents the best available method for preparing bromo-containing triethylsilyl and triethylgermyl enol ethers. NMR and IR spectral characteristic useful in the identification and characterization of these and related compounds are summarized.

Original language	English
Pages (from-to)	69-80
Number of pages	12
Journal	Journal of Organometallic Chemistry
Volume	201
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(00)92565-8
State	Published - 1 Jan 1980
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(00)92565-8

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title = "Silyl- and germylmercurials in organic synthesis. A new route to O-silylated and O-germylated enolates",

abstract = "The exchange reaction of α-mercurated ketones with bis(triethylsilyl)- (I) and bis(triethylgermyl)mercury (II) leads to the formation of the corresponding triethylsilyl and triethylgermyl enol ethers. O-Silylated and O-germylated enolates derived from ketones and aldehydes can be also prepared by treating mercurials I and II with appropriate α-bromo-carbonyl compounds. This new pathway also represents the best available method for preparing bromo-containing triethylsilyl and triethylgermyl enol ethers. NMR and IR spectral characteristic useful in the identification and characterization of these and related compounds are summarized.",

author = "Kruglaya, {O. A.} and Belousova, {L. I.} and Gendin, {D. V.} and Kalikhman, {I. D.} and Vyazankin, {N. S.}",

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T1 - Silyl- and germylmercurials in organic synthesis. A new route to O-silylated and O-germylated enolates

AU - Kruglaya, O. A.

AU - Belousova, L. I.

AU - Gendin, D. V.

AU - Kalikhman, I. D.

AU - Vyazankin, N. S.

PY - 1980/1/1

Y1 - 1980/1/1

N2 - The exchange reaction of α-mercurated ketones with bis(triethylsilyl)- (I) and bis(triethylgermyl)mercury (II) leads to the formation of the corresponding triethylsilyl and triethylgermyl enol ethers. O-Silylated and O-germylated enolates derived from ketones and aldehydes can be also prepared by treating mercurials I and II with appropriate α-bromo-carbonyl compounds. This new pathway also represents the best available method for preparing bromo-containing triethylsilyl and triethylgermyl enol ethers. NMR and IR spectral characteristic useful in the identification and characterization of these and related compounds are summarized.

AB - The exchange reaction of α-mercurated ketones with bis(triethylsilyl)- (I) and bis(triethylgermyl)mercury (II) leads to the formation of the corresponding triethylsilyl and triethylgermyl enol ethers. O-Silylated and O-germylated enolates derived from ketones and aldehydes can be also prepared by treating mercurials I and II with appropriate α-bromo-carbonyl compounds. This new pathway also represents the best available method for preparing bromo-containing triethylsilyl and triethylgermyl enol ethers. NMR and IR spectral characteristic useful in the identification and characterization of these and related compounds are summarized.

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Silyl- and germylmercurials in organic synthesis. A new route to O-silylated and O-germylated enolates

Abstract

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