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Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes

Siqueira, Fernanda A. (author)
Ishikawa, Eloisa E. (author)
Fogaça, André (author)
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Faccio, Andréa T. (author)
Carneiro, Vânia M. T. (author)
Soares, Rafael R. S. (author)
Utaka, Aline (author)
Tébéka, Iris R. M. (author)
Bielawski, Marcin (author)
Stockholms universitet,Institutionen för organisk kemi
Olofsson, Berit (author)
Stockholms universitet,Institutionen för organisk kemi
Silva Jr., Luiz F. (author)
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 (creator_code:org_t)
2011
2011
English.
In: Journal of the Brazilian Chemical Society. - 0103-5053 .- 1678-4790. ; 22:9, s. 1795-1807
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • 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.
  • 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.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

indanes
hypervalent iodine
ring contraction
1
2-dihydronaphthalenes
rearrangements
organisk kemi
Organic Chemistry

Publication and Content Type

ref (subject category)
art (subject category)

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