Radical-mediated cyclisation of ω-aryl-β-dicarbonyl compounds to tetrahydrobenzocyclohepten-6-ones, hexahydrobenzocycloocten-6-ones and naphthalen-2(1H)-ones

Joanne F. Jamie, Rodney W. Rickards*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Manganese(III) acetate in acetic acid promotes efficient radical-mediated oxidative cyclisation of ε-aryl-β-dicarbonyl and Z-γ,δ-unsaturated δ-aryl-β-dicarbonyl compounds carrying electron-releasing groups in the aromatic ring, forming 6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ones and naphthalen-2(1H)-ones, respectively. The process is accompanied by secondary acetoxylation at the activated benzylic position of the initial cyclisation products, and is exemplified by the conversions of the ε- and δ-aryl-β-dicarbonyl compounds 6 and 11 into the benzocycloheptenone 18 and the naphthalenone 21, respectively. Application of the oxidation to the formation of 8-membered hexahydro- and tetrahydro-benzocycloocten-6-ones 19 and 22 from ζ-aryl-β-dicarbonyl and Z-γ,δ-unsaturated ζ-aryl-β-dicarbonyl compounds is limited by low reactivity, and in the latter case, by radical rearrangement followed by cyclisation to a tetralin.

Original languageEnglish
Pages (from-to)3613-3621
Number of pages9
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number24
Publication statusPublished - 21 Dec 1997
Externally publishedYes

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