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Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)
Stockholm University, Faculty of Science, Department of Organic Chemistry. Universidade de São Paulo, Brazil.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2013 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 54, no 43, 5818-5820 p.Article in journal (Refereed) Published
Abstract [en]

A novel protocol for the oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) was developed. This approach uses inexpensive, readily available, and stable chemicals (PhI, mCPBA, and TsOH) giving rearrangement products in yields comparable to those obtained using the more expensive commercially available [hydroxy(tosyloxy)iodo]benzene [HTIB or Koser's reagent]. Additionally, an alternative protocol for the synthesis of 1-methyl-2-tetralone through the one-step epoxidation/rearrangement of 4-methyl-1,2-dihydronaphthalene using mCPBA and TsOH was developed.

Place, publisher, year, edition, pages
2013. Vol. 54, no 43, 5818-5820 p.
Keyword [en]
Rearrangement, Hypervalent iodine, Ring contraction, Oxidation, Alkenes
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-95415DOI: 10.1016/j.tetlet.2013.08.012ISI: 000325122100014OAI: oai:DiVA.org:su-95415DiVA: diva2:660876
Note

AuthorCount:5;

Available from: 2014-11-26 Created: 2013-10-28 Last updated: 2017-12-06Bibliographically approved

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