Synthesis of Dibenzo[a,e]cyclooctene-5,11(6H,12H)-diones via the Elusive Benzocyclobutenone Anion

Yingchao Huang; Jun Chen; Yu Liu; Ping Lu

doi:10.1055/a-1545-7706

Synthesis, Table of Contents

Synthesis 2021; 53(23): 4477-4483
DOI: 10.1055/a-1545-7706

paper

Synthesis of Dibenzo[a,e]cyclooctene-5,11(6H,12H)-diones via the Elusive Benzocyclobutenone Anion

Yingchao Huang

^aCollege of Chemistry and Life, Advanced Institute of Materials Science, Changchun University of Technology, Changchun 130012, P. R. of China

,

Jun Chen

^bDepartment of Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China

,

Yu Liu∗

^aCollege of Chemistry and Life, Advanced Institute of Materials Science, Changchun University of Technology, Changchun 130012, P. R. of China

,

Ping Lu ∗

^bDepartment of Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China

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Abstract

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Abstract

We reported here a facile synthesis of dibenzo[a,e]cyclooctene-5,11(6H,12H)-diones via dimerization of benzocyclobutenones in the presence of simple base via the elusive benzocyclobutenone anion. The temperature effect played a crucial role in the dimerization reaction. Further synthesis of 5,11-disubstituted dibenzo[a,e]cyclooctenes (dibenzo[a,e][8]annulenes) from dibenzo[a,e]cyclooctene-5,11(6H,12H)-diones was also explored.

Key words

benzocyclobutenone - dibenzo[a,e]cyclooctene-5,11-dione - dibenzo[a,e][8]annulene - carbon–carbon cleavage - dimerization - carbanions

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References

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