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DC Field | Value | Language |
---|---|---|
dc.contributor.author | Makhosazana, P. | - |
dc.contributor.author | Gamedze, Rejoice | - |
dc.contributor.author | Maseko, B | - |
dc.contributor.author | Chigondo, Fidelis | - |
dc.contributor.author | Nkambule, Comfort, M. | - |
dc.date.accessioned | 2016-04-26T16:45:58Z | - |
dc.date.available | 2016-04-26T16:45:58Z | - |
dc.date.issued | 2012 | - |
dc.identifier.issn | 0040-4039 | - |
dc.identifier.uri | http://dx.doi.org.access.msu.ac.zw:2048/10.1016/j.tetlet.2012.08.110 | - |
dc.description.abstract | The reaction of syn-1,2,4-triols under sulfonylation conditions catalyzed by Bu2SnO (5 mol %) results in cyclization and the formation of 3-hydroxy tetrahydrofurans (56–85%) while the anti-1,2,4-triols react to give C1-O-sulfonyl derivatives in good yields (66–83%) and the cyclization product in poor yield (5– 12%). A mechanism that justifies these observations is proposed to occur via the tosylation of the primary hydroxyl followed by an intramolecular tin acetal rearrangement to a 1,3-stannylene which then undergoes a 5-exo-tet-cyclization. The difference in rates of cyclization reactivity is due to the energetically more stable tin acetals of syn-1,3-diols compared to those of anti-1,3-diols. | en_US |
dc.language.iso | en | en_US |
dc.publisher | Elsevier | en_US |
dc.relation.ispartofseries | Tetrahedron Letters;Vol. 53, p. 5929–5932 | - |
dc.subject | Sulfonylation | en_US |
dc.subject | Tin acetal | en_US |
dc.subject | 1,2,4-Triols, 1,3-Diols | en_US |
dc.subject | Tetrahydrofurans | en_US |
dc.title | Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols | en_US |
dc.type | Article | en_US |
item.openairetype | Article | - |
item.grantfulltext | none | - |
item.fulltext | No Fulltext | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.languageiso639-1 | en | - |
item.cerifentitytype | Publications | - |
Appears in Collections: | Research Papers |
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