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• W2951649152 abstract "When arylmethyl 4-(sulfonyl)-3-butynyl ether and a catalytic amount of Rh2(tfa)4 (tfa = CF3CO2−) were heated in toluene, 2-aryl-3-(sulfonyl)-5,6-dihydro-2H-pyran was produced in good yield. Ring closure proceeded in a highly regioselective manner, and no isomeric five-membered product was detected. Alternatively, 2-(5-sulfonyl-4-pentynyl)tetrahydrofuran lacking a benzyl substituent afforded a different product, 9-sulfonyl-1-hydroxy-8-nonen-4-one, upon reaction with the same rhodium catalyst at reflux in wet toluene. Both reactions most likely involve cleavage of the C−H bond α to ether in the substrate and subsequent intramolecular transfer of the hydrogen atom to sulfonylacetylene, which is supported by experiments using deuterium-labeled starting materials." @default.
• W2951649152 created "2019-06-27" @default.
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• W2951649152 date "2009-02-11" @default.
• W2951649152 modified "2023-10-12" @default.
• W2951649152 title "Rh-Catalyzed Isomerization and Intramolecular Redox Reaction of Alkynyl Ethers Affording Dihydropyrans and Ketoolefins" @default.
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• W2951649152 doi "https://doi.org/10.1021/ja809826a" @default.
• W2951649152 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19209935" @default.
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