BAEYER-VILLIGER OXIDATION WITH Me3SiOOSiMe3 UNDER ASSISTANCE OF SnCl4 OR BF3-OEt2.

Seijiro Matsubara; Kazuhiko Takai; Hitosi Nozaki

doi:10.1246/bcsj.56.2029

BAEYER-VILLIGER OXIDATION WITH Me₃SiOOSiMe₃ UNDER ASSISTANCE OF SnCl₄ OR BF₃-OEt₂.

Seijiro Matsubara, Kazuhiko Takai, Hitosi Nozaki

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

40 Citations (Scopus)

Abstract

Treatment of ketones with bis(trimethylsilyl) peroxide and Lewis acid such as SnCl//4 or BF//3-OEt//2 in dichloromethane at room temperature affords esters in fair to excellent yields. Jasmine lactone is synthesized from 2- left bracket (Z)-pentenyl right bracket cyclopentanine by means of Me//3SiOOSiMe//3-BF//3-OEt//2 system without any protection of the carbon-carbon double bond. The oxidation of enol acetates of ketones to alpha -hydroxy (or alpha -acetoxy) ketones with Me//3SiOOSiMe//3-FeCl//3 system is also disclosed.

Original language	English
Pages (from-to)	2029-2032
Number of pages	4
Journal	Bulletin of the Chemical Society of Japan
Volume	56
Issue number	7
DOIs	https://doi.org/10.1246/bcsj.56.2029
Publication status	Published - Jan 1 1983
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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title = "BAEYER-VILLIGER OXIDATION WITH Me3SiOOSiMe3 UNDER ASSISTANCE OF SnCl4 OR BF3-OEt2.",

abstract = "Treatment of ketones with bis(trimethylsilyl) peroxide and Lewis acid such as SnCl//4 or BF//3-OEt//2 in dichloromethane at room temperature affords esters in fair to excellent yields. Jasmine lactone is synthesized from 2- left bracket (Z)-pentenyl right bracket cyclopentanine by means of Me//3SiOOSiMe//3-BF//3-OEt//2 system without any protection of the carbon-carbon double bond. The oxidation of enol acetates of ketones to alpha -hydroxy (or alpha -acetoxy) ketones with Me//3SiOOSiMe//3-FeCl//3 system is also disclosed.",

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year = "1983",

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T1 - BAEYER-VILLIGER OXIDATION WITH Me3SiOOSiMe3 UNDER ASSISTANCE OF SnCl4 OR BF3-OEt2.

AU - Matsubara, Seijiro

AU - Takai, Kazuhiko

AU - Nozaki, Hitosi

PY - 1983/1/1

Y1 - 1983/1/1

N2 - Treatment of ketones with bis(trimethylsilyl) peroxide and Lewis acid such as SnCl//4 or BF//3-OEt//2 in dichloromethane at room temperature affords esters in fair to excellent yields. Jasmine lactone is synthesized from 2- left bracket (Z)-pentenyl right bracket cyclopentanine by means of Me//3SiOOSiMe//3-BF//3-OEt//2 system without any protection of the carbon-carbon double bond. The oxidation of enol acetates of ketones to alpha -hydroxy (or alpha -acetoxy) ketones with Me//3SiOOSiMe//3-FeCl//3 system is also disclosed.

AB - Treatment of ketones with bis(trimethylsilyl) peroxide and Lewis acid such as SnCl//4 or BF//3-OEt//2 in dichloromethane at room temperature affords esters in fair to excellent yields. Jasmine lactone is synthesized from 2- left bracket (Z)-pentenyl right bracket cyclopentanine by means of Me//3SiOOSiMe//3-BF//3-OEt//2 system without any protection of the carbon-carbon double bond. The oxidation of enol acetates of ketones to alpha -hydroxy (or alpha -acetoxy) ketones with Me//3SiOOSiMe//3-FeCl//3 system is also disclosed.

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BAEYER-VILLIGER OXIDATION WITH Me₃SiOOSiMe₃ UNDER ASSISTANCE OF SnCl₄ OR BF₃-OEt₂.

Abstract

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