Tert-Butylnitrite as a convenient and easy-removable oxidant for the conversion of benzylic alcohols to ketones and aldehydes

Akiyuki Hamasaki; Hideyuki Kuwada; Makoto Tokunaga

doi:10.1016/j.tetlet.2011.12.006

Tert-Butylnitrite as a convenient and easy-removable oxidant for the conversion of benzylic alcohols to ketones and aldehydes

Akiyuki Hamasaki, Hideyuki Kuwada, Makoto Tokunaga

Multidisciplinary chemistry

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

19 Citations (Scopus)

Abstract

The oxidation of primary and secondary benzylic alcohols was achieved by using tert-butyl nitrite (t-BuONO) as a stoichiometric oxidant. Various substrates were effectively converted into the corresponding ketones or aldehydes in good to excellent yields. The reaction presumably proceeded by a nitrosyl exchange and a subsequent thermal decomposition of benzylic nitrites. This process would realize an oxidation of alcohols with oxygen in theory by combining with a reproduction of alkyl nitrites from NO and alcohols under an O ₂ atmosphere. In addition, almost pure oxidized products were readily obtained by simple evaporation of the reaction mixtures since t-BuONO produced only volatile side products.

Original language	English
Pages (from-to)	811-814
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2011.12.006
Publication status	Published - Feb 15 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.12.006

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title = "Tert-Butylnitrite as a convenient and easy-removable oxidant for the conversion of benzylic alcohols to ketones and aldehydes",

abstract = "The oxidation of primary and secondary benzylic alcohols was achieved by using tert-butyl nitrite (t-BuONO) as a stoichiometric oxidant. Various substrates were effectively converted into the corresponding ketones or aldehydes in good to excellent yields. The reaction presumably proceeded by a nitrosyl exchange and a subsequent thermal decomposition of benzylic nitrites. This process would realize an oxidation of alcohols with oxygen in theory by combining with a reproduction of alkyl nitrites from NO and alcohols under an O 2 atmosphere. In addition, almost pure oxidized products were readily obtained by simple evaporation of the reaction mixtures since t-BuONO produced only volatile side products.",

author = "Akiyuki Hamasaki and Hideyuki Kuwada and Makoto Tokunaga",

note = "Funding Information: This work was supported by a Grant-in-Aid for Global-COE program, {\textquoteleft}Science for Future Molecular Systems{\textquoteright}, and Scientific Research (A) (No. 20245014) from the Ministry of Education, Culture, Science, Sports and Technology of Japan. Appreciation also gose to Ube Industries, Ltd., for the financial support the company provided. We gratefully acknowledged Professor Tsutomu Katsuki of Kyushu University for providing use of a nitric oxide gas cylinder. ",

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T1 - Tert-Butylnitrite as a convenient and easy-removable oxidant for the conversion of benzylic alcohols to ketones and aldehydes

AU - Hamasaki, Akiyuki

AU - Kuwada, Hideyuki

AU - Tokunaga, Makoto

N1 - Funding Information: This work was supported by a Grant-in-Aid for Global-COE program, ‘Science for Future Molecular Systems’, and Scientific Research (A) (No. 20245014) from the Ministry of Education, Culture, Science, Sports and Technology of Japan. Appreciation also gose to Ube Industries, Ltd., for the financial support the company provided. We gratefully acknowledged Professor Tsutomu Katsuki of Kyushu University for providing use of a nitric oxide gas cylinder.

PY - 2012/2/15

Y1 - 2012/2/15

N2 - The oxidation of primary and secondary benzylic alcohols was achieved by using tert-butyl nitrite (t-BuONO) as a stoichiometric oxidant. Various substrates were effectively converted into the corresponding ketones or aldehydes in good to excellent yields. The reaction presumably proceeded by a nitrosyl exchange and a subsequent thermal decomposition of benzylic nitrites. This process would realize an oxidation of alcohols with oxygen in theory by combining with a reproduction of alkyl nitrites from NO and alcohols under an O 2 atmosphere. In addition, almost pure oxidized products were readily obtained by simple evaporation of the reaction mixtures since t-BuONO produced only volatile side products.

AB - The oxidation of primary and secondary benzylic alcohols was achieved by using tert-butyl nitrite (t-BuONO) as a stoichiometric oxidant. Various substrates were effectively converted into the corresponding ketones or aldehydes in good to excellent yields. The reaction presumably proceeded by a nitrosyl exchange and a subsequent thermal decomposition of benzylic nitrites. This process would realize an oxidation of alcohols with oxygen in theory by combining with a reproduction of alkyl nitrites from NO and alcohols under an O 2 atmosphere. In addition, almost pure oxidized products were readily obtained by simple evaporation of the reaction mixtures since t-BuONO produced only volatile side products.

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JO - Tetrahedron Letters

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ER -

Tert-Butylnitrite as a convenient and easy-removable oxidant for the conversion of benzylic alcohols to ketones and aldehydes

Abstract

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