Application of the Varrentrapp Reaction to the Preparation of Long-Chain Dicarboxylic Acids

Ackman, R. G.; Bannerman, M. A.; Retson, M. E.; Vandenheuvel, F. A.

doi:10.1139/v61-223

Can. J. Chem.

1961

DOI: 10.1139/v61-223

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Application of the Varrentrapp Reaction to the Preparation of Long-Chain Dicarboxylic Acids

R. G. Ackman¹,

M. A. Bannerman²,

M. E. Retson³

et al.

Abstract: not available

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Varrentrapp Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is a drastic alkaline degradation of the unsaturated carboxylic acids by fusion with alkali to give saturated carboxylic acids with at least two fewer carbon atoms, acetic acid, and hydrogen is generally referred to as the Varrentrapp reaction. Occasionally, it is also known as the Varrentrapp cleavage. It has been reported that for acids with only one double bond, the carboxylic acids of two carbon atoms fewer are formed, with yields usually > 90%. Besides the migration of the double bond in the Varrentrapp reaction, the carbon‐carbon triple bond also migrates under this condition, probably involving a reversible acetylene‐allene rearrangement. The saturated epoxy carboxylic acid undergoes the degradation too and the actual reaction path involving at least three different routes. Furthermore, an alkoxy moiety also undergoes a β‐elimination route during this reaction. This reaction has been found valuable for the industrial production of certain carboxylic acids.

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Varrentrapp Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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1997

Reaktionen Der Organischen Chemie

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Application of the Varrentrapp Reaction to the Preparation of Long-Chain Dicarboxylic Acids

Abstract: not available

Cited by 2 publications

References 0 publications

Varrentrapp Reaction

Varrentrapp Reaction

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