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dc.contributor.authorWu, CYen_US
dc.contributor.authorLin, HCen_US
dc.contributor.authorWang, ZYen_US
dc.contributor.authorWu, HJen_US
dc.date.accessioned2014-12-08T15:43:44Z-
dc.date.available2014-12-08T15:43:44Z-
dc.date.issued2001-06-29en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://dx.doi.org/10.1021/jo0100650en_US
dc.identifier.urihttp://hdl.handle.net/11536/29561-
dc.description.abstractThe synthesis of novel acetal this-cage compounds has been accomplished by the direct substitution for the oxygen atom by the sulfur atom in the reaction of the acetal groups of era-cages with Lawesson reagent (LR). Reaction of the tetraoxa-cage compound 2 with LR in dichloromethane at 25 degreesC sequentially gave the monothia-, dithia-, trithia-, and tetrathia-cage compounds 3, 6, 7, and 9. The reaction mechanism for the conversion from era-cages into thia-cages was proposed. The diacetal trioxa-cages 18-20 and 24-26 were also transformed into the thia-cages 21-23 and 27-29, respectively. Reaction of the trioxa-cages 34 and 35 with LR under the same reaction conditions gave the thia-cages 36 and 37 with the carbonyl group intact. Treatment of the pentaoxa[5]-peristylane 40 with LR in chloroform under supersonic shaking at refluxing temperature gave the monothia[5]peristylane 41 and the dithia-[5] peristylane 42. Attempts to synthesize the thia[5]-peristylanes from the tetraoxa-cage 51 and the transformation from the parent (unsubstituted) pentaoxa[5]peristylane 46 to the thia-cages have been made. Reaction of the pentaoxa[5]-peristylane 40 with P2S5 in refluxing toluene gave 41, 42, and a rearrangement product 47. The synthesis of new heterocyclic cage compounds 59 and 60, which contain oxygen, nitrogen, and sulfur atoms in the same molecule, was also accomplished.en_US
dc.language.isoen_USen_US
dc.titleSynthesis of novel acetal thia-cage compoundsen_US
dc.typeArticleen_US
dc.identifier.doi10.1021/jo0100650en_US
dc.identifier.journalJOURNAL OF ORGANIC CHEMISTRYen_US
dc.citation.volume66en_US
dc.citation.issue13en_US
dc.citation.spage4610en_US
dc.citation.epage4618en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000169536700019-
dc.citation.woscount15-
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