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dc.contributor.authorChi, CCen_US
dc.contributor.authorPai, IFen_US
dc.contributor.authorChung, WSen_US
dc.date.accessioned2014-12-08T15:37:17Z-
dc.date.available2014-12-08T15:37:17Z-
dc.date.issued2004-11-22en_US
dc.identifier.issn0040-4020en_US
dc.identifier.urihttp://dx.doi.org/10.1016/j.tet.2004.09.040en_US
dc.identifier.urihttp://hdl.handle.net/11536/25626-
dc.description.abstractRefluxing an o-dichlorobenzene solution of 2,5-disubstituted thienosultines 10a-f with [60]fullerene for 2-24 h gave both 1:1 and 2:1 cycloadducts in 37-79% isolated yields. The reaction was highly accelerated by microwave irradiation giving comparable yields of cycloadducts. Sultines 10a-f underwent cheletropic extrusion of SO2 to form the corresponding non-Kekule biradical intermediates 11a-f, which were subsequently trapped by [60]fullerene to form corresponding cycloadducts. The activation energy barriers (DeltaG(c)(not equal)) determined for the boat-to-boat inversion of these 4',5',6',7'-tetrahydrobenzo[c]thieno-[5',6':1,2][60]fullerene adducts 12a-f were found to be in the range of 13.5-14.8 kcal/mol. Unexpectedly, one of the monoadduct 12a was found to be labile when kept in air under ambient light. Two new products 15 (a sulfine-enone) and 16 (an endione) were isolated from the decomposed 12a and were found to derive from self-sensitized singlet oxygen reaction on the 2,5-dimethylthieno moiety of 12a. (C) 2004 Elsevier Ltd. All rights reserved.en_US
dc.language.isoen_USen_US
dc.subjectnon-Kekule biradicalen_US
dc.subjectTHE biradicalen_US
dc.subjectmicrowaveen_US
dc.subjectcycloadditionen_US
dc.subject[60]fullereneen_US
dc.subjectsinglet oxygen reactionen_US
dc.titleThermal and microwave assisted reactions of 2,5-disubstituted thienosultines with [60]fullerene: non-Kekule biradicals and self-sensitized oxygenation of the cycloadducten_US
dc.typeArticleen_US
dc.identifier.doi10.1016/j.tet.2004.09.040en_US
dc.identifier.journalTETRAHEDRONen_US
dc.citation.volume60en_US
dc.citation.issue48en_US
dc.citation.spage10869en_US
dc.citation.epage10876en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000224953200008-
dc.citation.woscount13-
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