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dc.contributor.authorWu, HJen_US
dc.contributor.authorYen, CHen_US
dc.contributor.authorChuang, CTen_US
dc.date.accessioned2014-12-08T15:48:53Z-
dc.date.available2014-12-08T15:48:53Z-
dc.date.issued1998-07-24en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/11536/32501-
dc.description.abstractThe intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.en_US
dc.language.isoen_USen_US
dc.titleIntramolecular Diels-Alder reaction of furans with allenyl ethers followed by sulfur and silicon atom-containing group rearrangementen_US
dc.typeArticleen_US
dc.identifier.journalJOURNAL OF ORGANIC CHEMISTRYen_US
dc.citation.volume63en_US
dc.citation.issue15en_US
dc.citation.spage5064en_US
dc.citation.epage5070en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000075263100027-
dc.citation.woscount20-
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