From aldehydes to nitriles, a general and high yielding transformation using HOF·CH3CN complex

Mira Carmeli; Neta Shefer; Shlomo Rozen

doi:10.1016/j.tetlet.2006.10.014

From aldehydes to nitriles, a general and high yielding transformation using HOF·CH₃CN complex

Mira Carmeli, Neta Shefer, Shlomo Rozen^*

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

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

29 Scopus citations

Abstract

N,N-Dimethylhydrazones of aldehydes undergo a rapid oxidative cleavage to form nitriles in very high yields on reaction with HOF·CH₃CN under mild conditions. The reaction is chemoselective and proceeds rapidly without racemization. The nitriles were resistant to further oxidation, even when a large excess of the reagent was employed.

Original language	English
Pages (from-to)	8969-8972
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2006.10.014
State	Published - 11 Dec 2006

Funding

Funders	Funder number
Israel Science Foundation

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10.1016/j.tetlet.2006.10.014

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title = "From aldehydes to nitriles, a general and high yielding transformation using HOF·CH3CN complex",

abstract = "N,N-Dimethylhydrazones of aldehydes undergo a rapid oxidative cleavage to form nitriles in very high yields on reaction with HOF·CH3CN under mild conditions. The reaction is chemoselective and proceeds rapidly without racemization. The nitriles were resistant to further oxidation, even when a large excess of the reagent was employed.",

author = "Mira Carmeli and Neta Shefer and Shlomo Rozen",

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AU - Carmeli, Mira

AU - Shefer, Neta

AU - Rozen, Shlomo

N1 - Funding Information: This work was supported by the Israel Science Foundation.

PY - 2006/12/11

Y1 - 2006/12/11

N2 - N,N-Dimethylhydrazones of aldehydes undergo a rapid oxidative cleavage to form nitriles in very high yields on reaction with HOF·CH3CN under mild conditions. The reaction is chemoselective and proceeds rapidly without racemization. The nitriles were resistant to further oxidation, even when a large excess of the reagent was employed.

AB - N,N-Dimethylhydrazones of aldehydes undergo a rapid oxidative cleavage to form nitriles in very high yields on reaction with HOF·CH3CN under mild conditions. The reaction is chemoselective and proceeds rapidly without racemization. The nitriles were resistant to further oxidation, even when a large excess of the reagent was employed.

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JO - Tetrahedron Letters

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ER -

From aldehydes to nitriles, a general and high yielding transformation using HOF·CH₃CN complex

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