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Metal-Free Synthesi...
Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes
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Siqueira, Fernanda A. (author)
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Ishikawa, Eloisa E. (author)
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Fogaça, André (author)
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Faccio, Andréa T. (author)
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Carneiro, Vânia M. T. (author)
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Soares, Rafael R. S. (author)
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Utaka, Aline (author)
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Tébéka, Iris R. M. (author)
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- Bielawski, Marcin (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Olofsson, Berit (author)
- Stockholms universitet,Institutionen för organisk kemi
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Silva Jr., Luiz F. (author)
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(creator_code:org_t)
- 2011
- 2011
- English.
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In: Journal of the Brazilian Chemical Society. - 0103-5053 .- 1678-4790. ; 22:9, s. 1795-1807
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https://su.diva-port... (primary) (Raw object)
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https://urn.kb.se/re...
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https://doi.org/10.1...
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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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- By the author/editor
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Siqueira, Fernan ...
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Ishikawa, Eloisa ...
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Fogaça, André
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Faccio, Andréa T ...
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Carneiro, Vânia ...
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Soares, Rafael R ...
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show more...
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Utaka, Aline
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Tébéka, Iris R. ...
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Bielawski, Marci ...
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Olofsson, Berit
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Silva Jr., Luiz ...
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show less...
- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Organic Chemistr ...
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Journal of the B ...
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Stockholm University