Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes (Articolo in rivista) (literal)

Anno

• 2006-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1016/j.tet.2005.11.010 (literal)

Alternative label

• Daquino C.; Foti M. C. (2006)
  Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes
  in Tetrahedron (Oxf., Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Daquino C.; Foti M. C. (literal)

Pagina inizio

• 1536 (literal)

Pagina fine

• 1547 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

• http://pdn.sciencedirect.com/science?_ob=MiamiImageURL&_cid=271372&_user=6691909&_pii=S0040402005019988&_check=y&_origin=search&_zone=rslt_list_item&_coverDate=2006-02-13&wchp=dGLbVlB-zSkzk&md5=d4add0d3a49cd083dff84aeb1b1b4ab8/1-s2.0-S0040402005019988-main.pdf (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 62 (literal)

Rivista

• Tetrahedron (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 7 (literal)

Note

• Scopu (literal)
• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Istituto di Chimica Biomolecolare del CNR - Sez. di Catania, Via del Santuario, 110, I-95028 Valverde (CT), Italy (literal)

Titolo

• Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes (literal)

Abstract

• The reaction at room temperature of 3,5-di-tert-butyl- and 3,5-di-methoxy-4-hydroxycinnamic acids 1 and 2 with the dpph% radical in acetone or other non-hydroxylic polar solvents yields interesting dimeric p-quinomethanes 10-16 characterized by a broad and strong absorption in the visible region. Although the yields appear to be low to moderate (10-40%), this simple synthesis affords quinones not otherwise obtainable, which contain an unsaturated g-lactone ring (14-16). The structures have been elucidated by interpretation of ESI-MS, FT-IR and NMR spectral data. In particular, FT-IR spectra in a KBr matrix demonstrate the quinone nature of these compounds because of the presence of strong absorption bands at 1604-1640 cmK1 and allows excluding the presence of carboxylic acid groups in the molecules. Kinetic evidence and molecular structures suggest that the formation of these p-quinomethanes is best explained through an 8-8 C-C coupling of the aryloxyl radicals derived from 1 and 2 and a subsequent fast mono- or di-decarboxylation of the initial dimer by an SE1-type mechanism. Further oxidation of the phenolic intermediates by dpph% yields the final quinones. (literal)

Prodotto di

• Antiossidanti per uso farmaceutico, cosmetico e alimentare (PM.P01.010.001) (Modulo)
• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR

• MARIO CONCETTO FOTI (Unità di personale interno)
• CARMELO DAQUINO (Unità di personale esterno)

Insieme di parole chiave

• Parole chiave di "Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• MARIO CONCETTO FOTI (Unità di personale interno)
• CARMELO DAQUINO (Unità di personale esterno)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Antiossidanti per uso farmaceutico, cosmetico e alimentare (PM.P01.010.001) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Tetrahedron (Rivista)

Insieme di parole chiave di

• Parole chiave di "Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes" (Insieme di parole chiave)