Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates

Pavel A. Krasutsky; Igor V. Kolomitsyn; Evgenij M. Botov; Robert M. Carlson; Irina G. Semenova; Andrey A. Fokin

doi:10.1016/S0040-4039(02)02151-2

Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates

Pavel A. Krasutsky, Igor V. Kolomitsyn, Evgenij M. Botov, Robert M. Carlson, Irina G. Semenova, Andrey A. Fokin

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Abstract

Selective carboxylic acid decarboxylation was elaborated. Generation of acyltrifluoroacetyl peroxides from carboxylic peracids and trifluoroacetyl anhydride (Method A), as well as from trifluoroperacetic acid and acyltrifluoroacetyl anhydride (Method B), leads to simultaneous peroxide decomposition into the corresponding alkyltrifluoroacetates. DFT computations, as well as experimental data, support an acid-catalyzed heterolytic mechanism for acyltrifluoroacetyl peroxide decomposition.

Original language	English (US)
Pages (from-to)	8687-8691
Number of pages	5
Journal	Tetrahedron Letters
Volume	43
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(02)02151-2
State	Published - Nov 25 2002

Bibliographical note

Funding Information:
A portion of this work was supported by the International Soros Foundation (Reg # иCC000). We are also grateful to the US Civilian Research and Development Foundation (CRDF) for Travel Grant (TGP-438 for A.A.F.) and to Dr. Nico J. R. van Eikema Hommes (University Erlangen-Nürnberg) for the use of the ‘Molecule’ program.

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title = "Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates",

abstract = "Selective carboxylic acid decarboxylation was elaborated. Generation of acyltrifluoroacetyl peroxides from carboxylic peracids and trifluoroacetyl anhydride (Method A), as well as from trifluoroperacetic acid and acyltrifluoroacetyl anhydride (Method B), leads to simultaneous peroxide decomposition into the corresponding alkyltrifluoroacetates. DFT computations, as well as experimental data, support an acid-catalyzed heterolytic mechanism for acyltrifluoroacetyl peroxide decomposition.",

author = "Krasutsky, {Pavel A.} and Kolomitsyn, {Igor V.} and Botov, {Evgenij M.} and Carlson, {Robert M.} and Semenova, {Irina G.} and Fokin, {Andrey A.}",

note = "Funding Information: A portion of this work was supported by the International Soros Foundation (Reg # иCC000). We are also grateful to the US Civilian Research and Development Foundation (CRDF) for Travel Grant (TGP-438 for A.A.F.) and to Dr. Nico J. R. van Eikema Hommes (University Erlangen-N{\"u}rnberg) for the use of the {\textquoteleft}Molecule{\textquoteright} program.",

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T1 - Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates

AU - Krasutsky, Pavel A.

AU - Kolomitsyn, Igor V.

AU - Botov, Evgenij M.

AU - Carlson, Robert M.

AU - Semenova, Irina G.

AU - Fokin, Andrey A.

N1 - Funding Information: A portion of this work was supported by the International Soros Foundation (Reg # иCC000). We are also grateful to the US Civilian Research and Development Foundation (CRDF) for Travel Grant (TGP-438 for A.A.F.) and to Dr. Nico J. R. van Eikema Hommes (University Erlangen-Nürnberg) for the use of the ‘Molecule’ program.

PY - 2002/11/25

Y1 - 2002/11/25

N2 - Selective carboxylic acid decarboxylation was elaborated. Generation of acyltrifluoroacetyl peroxides from carboxylic peracids and trifluoroacetyl anhydride (Method A), as well as from trifluoroperacetic acid and acyltrifluoroacetyl anhydride (Method B), leads to simultaneous peroxide decomposition into the corresponding alkyltrifluoroacetates. DFT computations, as well as experimental data, support an acid-catalyzed heterolytic mechanism for acyltrifluoroacetyl peroxide decomposition.

AB - Selective carboxylic acid decarboxylation was elaborated. Generation of acyltrifluoroacetyl peroxides from carboxylic peracids and trifluoroacetyl anhydride (Method A), as well as from trifluoroperacetic acid and acyltrifluoroacetyl anhydride (Method B), leads to simultaneous peroxide decomposition into the corresponding alkyltrifluoroacetates. DFT computations, as well as experimental data, support an acid-catalyzed heterolytic mechanism for acyltrifluoroacetyl peroxide decomposition.

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U2 - 10.1016/S0040-4039(02)02151-2

DO - 10.1016/S0040-4039(02)02151-2

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EP - 8691

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates

Abstract

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