Oxidative decarboxylation of mandelate ethers and α-substituted phenylacetates via dioxetanone generation

Bertrand Heckmann; Carole Alayrac; Charges Mioskowski; S. Chandrasekhar; J. R. Falck

doi:10.1016/S0040-4039(00)79133-7

Oxidative decarboxylation of mandelate ethers and α-substituted phenylacetates via dioxetanone generation

Bertrand Heckmann, Carole Alayrac, Charges Mioskowski, S. Chandrasekhar, J. R. Falck

Biochemistry

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

7 Scopus citations

Abstract

Mandelate ethers are oxidatively decarboxylated via in situ generated dioxetanones using ^tBuOK and air at ambient temperature leading, after hydrolysis, to the benzoic acid and the corresponding alcohol. The reaction can be extended to α-substituted phenylacetates.

Original language	English (US)
Pages (from-to)	5205-5208
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(00)79133-7
State	Published - Sep 1 1992

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)79133-7

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title = "Oxidative decarboxylation of mandelate ethers and α-substituted phenylacetates via dioxetanone generation",

abstract = "Mandelate ethers are oxidatively decarboxylated via in situ generated dioxetanones using tBuOK and air at ambient temperature leading, after hydrolysis, to the benzoic acid and the corresponding alcohol. The reaction can be extended to α-substituted phenylacetates.",

author = "Bertrand Heckmann and Carole Alayrac and Charges Mioskowski and S. Chandrasekhar and Falck, {J. R.}",

note = "Funding Information: Acknowledgment: We thankt heCNRS, Rhone-PoulencA grochimie,U SPHS NIH (DK-38226),a nd the Robert A. Welch Foundation (I-782) for financial support.F unds for the purchaseo f a mass spectrometwere rep rovidedb y NlH (SIO RR05922).",

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doi = "10.1016/S0040-4039(00)79133-7",

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T1 - Oxidative decarboxylation of mandelate ethers and α-substituted phenylacetates via dioxetanone generation

AU - Heckmann, Bertrand

AU - Alayrac, Carole

AU - Mioskowski, Charges

AU - Chandrasekhar, S.

AU - Falck, J. R.

N1 - Funding Information: Acknowledgment: We thankt heCNRS, Rhone-PoulencA grochimie,U SPHS NIH (DK-38226),a nd the Robert A. Welch Foundation (I-782) for financial support.F unds for the purchaseo f a mass spectrometwere rep rovidedb y NlH (SIO RR05922).

PY - 1992/9/1

Y1 - 1992/9/1

N2 - Mandelate ethers are oxidatively decarboxylated via in situ generated dioxetanones using tBuOK and air at ambient temperature leading, after hydrolysis, to the benzoic acid and the corresponding alcohol. The reaction can be extended to α-substituted phenylacetates.

AB - Mandelate ethers are oxidatively decarboxylated via in situ generated dioxetanones using tBuOK and air at ambient temperature leading, after hydrolysis, to the benzoic acid and the corresponding alcohol. The reaction can be extended to α-substituted phenylacetates.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Oxidative decarboxylation of mandelate ethers and α-substituted phenylacetates via dioxetanone generation

Abstract

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