In situ generation of hydroperoxide by oxidation of benzhydrols to benzophenones using sodium hydride under oxygen atmosphere: Use for the oxidative cleavage of cyclic 1,2-diketones to dicarboxylic acids

Sunhae Kang; Soyoung Lee; Minju Jeon; Sun Min Kim; Young Sug Kim; Hogyu Han; Jung Woon Yang

doi:10.1016/j.tetlet.2012.10.127

In situ generation of hydroperoxide by oxidation of benzhydrols to benzophenones using sodium hydride under oxygen atmosphere: Use for the oxidative cleavage of cyclic 1,2-diketones to dicarboxylic acids

Sunhae Kang
, Soyoung Lee
, Minju Jeon
, Sun Min Kim
, Young Sug Kim
, Hogyu Han^*
, Jung Woon Yang

^*Corresponding author for this work

College of Science

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

14 Citations (Scopus)

Abstract

A facile oxidative cleavage of cyclic 1,2-diketones 1 to dicarboxylic acids 3 with hydroperoxide generated in situ has been developed. In situ generation of hydroperoxide was effected by the oxidation of 4,4′-dichlorobenzhydrol 2f to 4,4′-dichlorobenzophenone 4f using sodium hydride under oxygen atmosphere.

Original language	English
Pages (from-to)	373-376
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2012.10.127
Publication status	Published - 2013 Jan 30

Keywords

Benzhydrol
Cyclic 1,2-diketone
Dicarboxylic acid
Oxidative cleavage
Sodium hydride

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.10.127

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Kang, S., Lee, S., Jeon, M., Kim, S. M., Kim, Y. S., Han, H., & Yang, J. W. (2013). In situ generation of hydroperoxide by oxidation of benzhydrols to benzophenones using sodium hydride under oxygen atmosphere: Use for the oxidative cleavage of cyclic 1,2-diketones to dicarboxylic acids. Tetrahedron Letters, 54(5), 373-376. https://doi.org/10.1016/j.tetlet.2012.10.127

In situ generation of hydroperoxide by oxidation of benzhydrols to benzophenones using sodium hydride under oxygen atmosphere: Use for the oxidative cleavage of cyclic 1,2-diketones to dicarboxylic acids. / Kang, Sunhae; Lee, Soyoung; Jeon, Minju et al.
In: Tetrahedron Letters, Vol. 54, No. 5, 30.01.2013, p. 373-376.

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

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abstract = "A facile oxidative cleavage of cyclic 1,2-diketones 1 to dicarboxylic acids 3 with hydroperoxide generated in situ has been developed. In situ generation of hydroperoxide was effected by the oxidation of 4,4′-dichlorobenzhydrol 2f to 4,4′-dichlorobenzophenone 4f using sodium hydride under oxygen atmosphere.",

keywords = "Benzhydrol, Cyclic 1,2-diketone, Dicarboxylic acid, Oxidative cleavage, Sodium hydride",

author = "Sunhae Kang and Soyoung Lee and Minju Jeon and Kim, \{Sun Min\} and Kim, \{Young Sug\} and Hogyu Han and Yang, \{Jung Woon\}",

year = "2013",

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doi = "10.1016/j.tetlet.2012.10.127",

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T2 - Use for the oxidative cleavage of cyclic 1,2-diketones to dicarboxylic acids

AU - Kang, Sunhae

AU - Lee, Soyoung

AU - Jeon, Minju

AU - Kim, Sun Min

AU - Kim, Young Sug

AU - Han, Hogyu

AU - Yang, Jung Woon

PY - 2013/1/30

Y1 - 2013/1/30

N2 - A facile oxidative cleavage of cyclic 1,2-diketones 1 to dicarboxylic acids 3 with hydroperoxide generated in situ has been developed. In situ generation of hydroperoxide was effected by the oxidation of 4,4′-dichlorobenzhydrol 2f to 4,4′-dichlorobenzophenone 4f using sodium hydride under oxygen atmosphere.

AB - A facile oxidative cleavage of cyclic 1,2-diketones 1 to dicarboxylic acids 3 with hydroperoxide generated in situ has been developed. In situ generation of hydroperoxide was effected by the oxidation of 4,4′-dichlorobenzhydrol 2f to 4,4′-dichlorobenzophenone 4f using sodium hydride under oxygen atmosphere.

KW - Benzhydrol

KW - Cyclic 1,2-diketone

KW - Dicarboxylic acid

KW - Oxidative cleavage

KW - Sodium hydride

UR - https://www.scopus.com/pages/publications/84871264343

U2 - 10.1016/j.tetlet.2012.10.127

DO - 10.1016/j.tetlet.2012.10.127

M3 - Article

AN - SCOPUS:84871264343

SN - 0040-4039

VL - 54

SP - 373

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

In situ generation of hydroperoxide by oxidation of benzhydrols to benzophenones using sodium hydride under oxygen atmosphere: Use for the oxidative cleavage of cyclic 1,2-diketones to dicarboxylic acids

Abstract

Keywords

ASJC Scopus subject areas

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