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

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

Publikationsverlauf

Eingereicht: 29. März 2021

Angenommen nach Revision: 07. Juli 2021

Accepted Manuscript online:
07. Juli 2021

Artikel online veröffentlicht:
25. August 2021

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