Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | WU, HJ | en_US |
dc.contributor.author | LIN, CC | en_US |
dc.date.accessioned | 2014-12-08T15:03:04Z | - |
dc.date.available | 2014-12-08T15:03:04Z | - |
dc.date.issued | 1995-11-17 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | http://hdl.handle.net/11536/1648 | - |
dc.description.abstract | Several novel tetraacetal era-cage compounds 5a-d and convex tetraquinane era-cage compounds 16a-d and 17b-d are synthesized from alkylfurans in three steps. Ozonolysis of the cis-endo-1,4-diones 3a-d in dichloromethane at -78 degrees C followed by reduction with dimethyl sulfide gives the era-cages 5a-d in high yields, respectively. The structures of these new tetraacetal era-cages are deduced from their spectral data and proven for the first time by X-ray analysis of the crystalline compound 5a. Ozonolysis of 3a-d in dichloromethane at -78 degrees C followed by treatment with triethylamine gives the convex tetraquinane era-cages 16a-d and 17b-d in 85-90% yields, respectively. The structures of these novel convex tetraquinane era-cages are finally proven by X-ray analysis of the crystalline compound 16a. Two reaction mechanisms via the common final ozonides are proposed for the formation of these two different types of era-cage compounds. The structures of the final ozonides formed by ozonolysis of the norbornene derivatives 3 are deduced to be 9 with endo stereochemistry on the basis of their spectral data and the formation of these two types of era-cages from the final ozonides. In reaction with the final ozonides, triethylamine is found to act as a base instead of a reducing agent, a different function from that of dimethyl sulfide. The synthesis of era-cages 24 and 25, which possess aromatic substituents directly on the skeleton, has also been accomplished. | en_US |
dc.language.iso | en_US | en_US |
dc.title | NOVEL OXA-CAGE COMPOUNDS - SYNTHESIS, STRUCTURES, AND THE FORMATION MECHANISM OF TETRAACETAL OXA-CAGES AND CONVEX TETRAQUINANE OXA-CAGES | en_US |
dc.type | Article | en_US |
dc.identifier.journal | JOURNAL OF ORGANIC CHEMISTRY | en_US |
dc.citation.volume | 60 | en_US |
dc.citation.issue | 23 | en_US |
dc.citation.spage | 7558 | en_US |
dc.citation.epage | 7566 | en_US |
dc.contributor.department | 交大名義發表 | zh_TW |
dc.contributor.department | 應用化學系 | zh_TW |
dc.contributor.department | National Chiao Tung University | en_US |
dc.contributor.department | Department of Applied Chemistry | en_US |
dc.identifier.wosnumber | WOS:A1995TF69900031 | - |
dc.citation.woscount | 38 | - |
Appears in Collections: | Articles |
Files in This Item:
If it is a zip file, please download the file and unzip it, then open index.html in a browser to view the full text content.