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Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes
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2011 (English)In: Journal of the Brazilian Chemical Society, ISSN 0103-5053, E-ISSN 1678-4790, Vol. 22, no 9, 1795-1807 p.Article in journal (Refereed) Published
Abstract [en]

A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH)OTs (HTIB or Koser’s reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.

Abstract [pt]

Um protocolo livre de metais foi desenvolvido para sintetizar indanos através da contração de anel de 1,2-di-hidronaftalenos promovida por PhI(OH)OTs (HTIB ou reagente de Koser). Este rearranjo oxidativo pode ser realizado em diversos solventes (MeOH, CH3CN, 2,2,2-trifluoroetanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), e uma mistura 1:4 de TFE:CH2Cl2) em condições brandas. A contração de anel fornece indanos trans-1,3-dissubstituídos diastereosseletivamente, os quais são difíceis de obter em química orgânica sintética.

Place, publisher, year, edition, pages
2011. Vol. 22, no 9, 1795-1807 p.
Keyword [en]
indanes, hypervalent iodine, ring contraction, 1, 2-dihydronaphthalenes, rearrangements
National Category
Organic Chemistry
Research subject
Organic Chemistry
URN: urn:nbn:se:su:diva-62493DOI: 10.1590/S0103-50532011000900024ISI: 000295800700024OAI: diva2:442337
Available from: 2011-09-21 Created: 2011-09-21 Last updated: 2014-10-29Bibliographically approved

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Bielawski, MarcinOlofsson, Berit
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