Type 2 Ring-Opening Reactions of Cyclopropanated 7-Oxabenzonorbornadienes under Acid Catalysis

Tigchelaar, Andrew; Haner, Jamie; Carlson, Emily; Tam, William

doi:10.1055/s-0034-1378581

Cited by 9 publications

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“…Under thermal conditions, the dihydronaphthalenols can fully aromatize to form various substituted naphthalene derivatives 11 . This has been accomplished through acid catalysis with various alcohol nucleophiles [31]. The last type of predicted ring opening (type 3) which has not yet been observed involves the attack of the nucleophile at the internal cyclopropane carbon C, which could induce ring expansion to form seven-membered ring 12 .…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene with alcohols

Tait¹,

Al-Rifai²,

Boutin³

et al. 2016

Beilstein J. Org. Chem.

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SummaryPalladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene derivatives using alcohol nucleophiles were investigated. The optimal conditions were found to be 10 mol % PdCl2(CH3CN)2 in methanol, offering yields up to 92%. The reaction was successful using primary, secondary and tertiary alcohol nucleophiles and was compatible with a variety of substituents on cyclopropanated oxabenzonorbornadiene. With unsymmetrical C1-substituted cyclopropanated 7-oxabenzonorbornadienes, the regioselectivity of the reaction was excellent, forming only one regioisomer in all cases.

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Section: Introductionmentioning

confidence: 99%