Concerning the Reactivity of Dioxiranes. Observations from Experiments and Theory (Articolo in rivista)

Type

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

Label

• Concerning the Reactivity of Dioxiranes. Observations from Experiments and Theory (Articolo in rivista) (literal)

Anno

• 2008-01-01T00:00:00+01:00 (literal)

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

• 10.1021/ja075068u (literal)

Alternative label

• Annese C.; D'Accolti L.; Dinoi A.; Fusco C.; Gandolfi R.; Curci R. (2008)
  Concerning the Reactivity of Dioxiranes. Observations from Experiments and Theory
  in Journal of the American Chemical Society (Print)
  (literal)

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

• Annese C.; D'Accolti L.; Dinoi A.; Fusco C.; Gandolfi R.; Curci R. (literal)

Pagina inizio

• 1197 (literal)

Pagina fine

• 1204 (literal)

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

• 130 (literal)

Rivista

• Journal of the American Chemical Society (Rivista)

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

• 8 (literal)

Note

• ISI Web of Science (WOS) (literal)

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

• Dipartimento Chimica, Università di Bari, CNR.-ICCOM and Università di Pavia (literal)

Titolo

• Concerning the Reactivity of Dioxiranes. Observations from Experiments and Theory (literal)

Abstract

• The challenging hypothesis of a \"biphilic\" (i.e., electrophilic vs nucleophilic) character for dioxirane reactivity, which envisages that electron-poor alkenes are attacked by dioxiranes in a nucleophilic fashion, could not be sustained exptl. Rate data, which est. Hammett ? values for the epoxidn. of 3- or 4-substituted cinnamonitriles X·Ph-CH:CH-CN, unequivocally allow one to establish that dioxiranes epoxidize electrophilically even alkenes carrying electron-withdrawing groups. The greater propensity of methyl(trifluoromethyl)dioxirane TFDO (1b) to act as an electrophilic oxidant with respect to dimethyldioxirane DDO (1a) parallels the cathode redn. potentials for the two dioxiranes, as measured by cyclic voltammetry. A simple FMO approach for alkene epoxidn. is helpful to conceive a likely rationale for the greater oxidizing power of TFDO as compared to DDO. (literal)

Prodotto di

• processi e metodologie sostenibili in chimica organica per la sintesi di nuove piattaforme molecolari (PM.P03.011.001) (Modulo)
• Institute of chemistry of organometallic compounds (ICCOM) (Istituto)

Autore CNR

• CATERINA FUSCO (Persona)

Incoming links:

Prodotto

• Institute of chemistry of organometallic compounds (ICCOM) (Istituto)
• processi e metodologie sostenibili in chimica organica per la sintesi di nuove piattaforme molecolari (PM.P03.011.001) (Modulo)

Autore CNR di

• CATERINA FUSCO (Persona)

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

• Journal of the American Chemical Society (Rivista)