Formation of an unexpected rearrangement product using Grubbs' second generation catalyst: 2-allyl-3,4-dihydro-2H-1,4-benzothiazines from diene precursors

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dc.contributor.authorMorgans G.L.
dc.contributor.authorYadav D.B.
dc.contributor.authorFernandes M.A.
dc.contributor.authorDe Koning C.B.
dc.contributor.authorMichael J.P.
dc.contributor.authorVan Otterlo W.A.L.
dc.date.accessioned2012-04-20T07:09:22Z
dc.date.available2012-04-20T07:09:22Z
dc.date.issued2012
dc.description.abstractApplication of sub-stoichiometric amounts of Grubbs' second generation catalyst to the substrate N-allyl-N-[2-(allylsulfanyl)phenyl]-4- methylbenzenesulfonamide afforded the ring-closed compound 6-[(4-methylphenyl) sulfonyl]-5,6-dihydro-2H-1,6-benzothiazocine, as well as the unexpected 2-allyl-4-[(4-methylphenyl)sulfonyl]-3,4-dihydro-2H-1,4-benzothiazine. Use of similar conditions on an analogous sulfoxide resulted in the expected product, 6-[(4-methylphenyl)sulfonyl]-5,6-dihydro-2H-1,6-benzothiazocine 1-oxide, indicating that the sulfide was playing a key role in this novel transformation. Furthermore, the use of N-allyl-4-methyl-N-{2-[(2-methyl-2-propenyl)sulfanyl] phenyl}-benzenesulfonamide in the same reaction gave 2-(2-methyl-2-propenyl)-3, 4-dihydro-2H-1,4-benzothiazine. © 2012 Elsevier Ltd. All rights reserved.
dc.identifier.citationTetrahedron Letters
dc.identifier.citation53
dc.identifier.citation19
dc.identifier.citation2384
dc.identifier.citation2387
dc.identifier.issn404039
dc.identifier.other10.1016/j.tetlet.2012.02.109
dc.identifier.urihttp://hdl.handle.net/10019.1/20805
dc.subjectBenzothiazine
dc.subjectBenzothiazocine
dc.subjectRearrangements
dc.subjectRing-closing metathesis
dc.subjectRuthenium carbene
dc.titleFormation of an unexpected rearrangement product using Grubbs' second generation catalyst: 2-allyl-3,4-dihydro-2H-1,4-benzothiazines from diene precursors
dc.typeArticle
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