Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

Denis D. Borisov; Grigorii R. Chermashentsev; Roman A. Novikov; Yury V. Tomilov

doi:10.1055/a-1348-4311

Synthesis, Table of Contents

Synthesis 2021; 53(13): 2253-2259
DOI: 10.1055/a-1348-4311

paper

Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

Denis D. Borisov

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

,

Grigorii R. Chermashentsev

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

^bDepartment of Chemistry, Lomonosov Moscow State University, 1 Leninskie Gory, 119991 Moscow, Russian Federation

,

Roman A. Novikov∗

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

,

Yury V. Tomilov∗

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

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Abstract

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Abstract

A method has been developed for the synthesis of substituted β-styrylmalonates by conversion of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) in the presence of gallium trichloride into the corresponding 1,2-zwitterionic intermediates or (2-arylethylidene)malonates, followed by treatment with pyridine at room temperature leading to an isomerization of the emerging double bond. This method allows one to expand these reactions to include ACDCs with acceptor substituents at the aromatic ring.

Key words

donor-acceptor cyclopropanes - (2-arylethylidene)malonates - β-styrylmalonates - gallium trichloride - isomerization

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References

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