Publication
Saccharin derivative synthesis via [1,3] thermal sigmatropic rearrangement: a multistep organic chemistry experiment for undergraduate students
| dc.contributor.author | Fonseca, Custódia | |
| dc.date.accessioned | 2017-04-07T15:55:56Z | |
| dc.date.available | 2017-04-07T15:55:56Z | |
| dc.date.issued | 2016-10 | |
| dc.description.abstract | Saccharin (1,2-benzisothiazole-3-one 1,1-dioxide) is an artificial sweetener used in the food industry. It is a cheap and easily available organic compound that may be used in organic chemistry laboratory classes for the synthesis of related heterocyclic compounds and as a derivatizing agent. In this work, saccharin is used as a starting material in a sequential synthesis designed for completion in three laboratory periods of 4 h each. This synthesis includes two nucleophilic substitutions, namely, the transformation of saccharin into saccharyl chloride and the addition of cinnamyl alcohol to saccharyl chloride (3-chloro-1,2-benzisothiazole 1,1-dioxide) to yield O-cinnamylsaccharin [(E)-3-(3-phenylprop-2-enoxy)-1,2-benzisothiazole 1,1-dioxide]. The third reaction is the isomerization of O-cinnamylsaccharin into N-cinnamylsacchain [2-(3-pheny1-2(E)-propen-1-yl)]-1,2-benzisothiazole-3(2H)-one 1,1-dioxide], a [1,3] sigmatropic rearrangement. The products are characterized using melting point, IR, and H-1 NMR spectroscopy. These experiments allow students to acquire experience in a multistep synthesis, practice the most typical laboratory scale synthesis, isolation, purification, and analytical methods, and think through and discuss the mechanisms of the intervening reactions. | |
| dc.identifier.doi | 10.1021/acs.jchemed.6b00046 | |
| dc.identifier.issn | 0021-9584 | |
| dc.identifier.other | AUT: CFO00714; | |
| dc.identifier.uri | http://hdl.handle.net/10400.1/9263 | |
| dc.language.iso | eng | |
| dc.peerreviewed | yes | |
| dc.relation.isbasedon | WOS:000385903100016 | |
| dc.title | Saccharin derivative synthesis via [1,3] thermal sigmatropic rearrangement: a multistep organic chemistry experiment for undergraduate students | |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 1784 | |
| oaire.citation.issue | 10 | |
| oaire.citation.startPage | 1781 | |
| oaire.citation.title | Journal of Chemical Education | |
| oaire.citation.volume | 93 | |
| person.familyName | Fonseca | |
| person.givenName | Custódia | |
| person.identifier.ciencia-id | 601F-8F41-D5E4 | |
| person.identifier.orcid | 0000-0002-2480-3364 | |
| rcaap.rights | openAccess | |
| rcaap.type | article | |
| relation.isAuthorOfPublication | 30b7964c-964a-4ed0-bb05-594361e50df7 | |
| relation.isAuthorOfPublication.latestForDiscovery | 30b7964c-964a-4ed0-bb05-594361e50df7 |
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