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The treatment of dimethoxy[n]paracyclophanes (n = 7–12) (5), [2]paracyclo[2]thiophenophane (13), and dimethoxy[2.2]paracyclophane (8) with CAN in MeCN–water afforded 2,4-cyclohexadien-1-ones 9, [8]paracyclophanedione 10, the ring-opened esters 11, and ketones 12. When the n value of 5 was 7, 8, or 9, rearrangement of the methylene bridge occurred and 9 was obtained as the main products. With the n value of 12, quinone 10 was the main product. Whereas, treatment of 13 with CAN afforded the ring-opened ester 14 as the sole product. These results show that formation of 9 is dependent on the strain of the paracyclophanes. Epoxide A was proposed as an intermediate of these reactions.

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Application of Lanthanoids to Organic Chemistry. Direct Alkoxylation of Anthracene

Sugiyama¹

1987

Chemistry Letters

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Cited by 3 publications

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Lanthanides in Organic Synthesis

Lanthanides in Organic Synthesis

Treatment of Dimethoxyparacyclophanes with Ammonium Cerium(IV) Nitrate

Application of Lanthanoids to Organic Chemistry. Direct Alkoxylation of Anthracene

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