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Synthesis 2021; 53(23): 4477-4483
DOI: 10.1055/a-1545-7706
DOI: 10.1055/a-1545-7706
paper
Synthesis of Dibenzo[a,e]cyclooctene-5,11(6H,12H)-diones via the Elusive Benzocyclobutenone Anion
This work was supported by the National Natural Science Foundation of China (Nos. 22071028, 21772024, and 21921003).
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 - carbanionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1545-7706.
- Supporting Information
Publication History
Received: 29 March 2021
Accepted after revision: 07 July 2021
Accepted Manuscript online:
07 July 2021
Article published online:
25 August 2021
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