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Titolo:
Electron transfer catalyzed [2+2] cycloreversion of benzene dimers
Autore:
Reddy, GD; Wiest, O; Hudlicky, T; Schapiro, V; Gonzalez, D;
Indirizzi:
Univ Florida, Dept Chem, Gainesville, FL 32611 USA Univ Florida Gainesville FL USA 32611 ept Chem, Gainesville, FL 32611 USA Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA Univ Notre Dame Notre Dame IN USA 46556 Biochem, Notre Dame, IN 46556 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 8, volume: 64, anno: 1999,
pagine: 2860 - 2863
SICI:
0022-3263(19990416)64:8<2860:ETC[CO>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
THROUGH-BOND INTERACTION; RADICAL-CATION; DNA PHOTOLYASE; CHEMISTRY; MOLECULES; CLEAVAGE; REPAIR;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
37
Recensione:
Indirizzi per estratti:
Indirizzo: Wiest, O Univ Florida, Dept Chem, Gainesville, FL 32611 USA Univ Florida Gainesville FL USA 32611 Gainesville, FL 32611 USA
Citazione:
G.D. Reddy et al., "Electron transfer catalyzed [2+2] cycloreversion of benzene dimers", J ORG CHEM, 64(8), 1999, pp. 2860-2863

Abstract

The catalysis of the [2 + 2] cycloreversion of the anti-o,o'-benzene dimer1 and the syn-o,o'-naphthalene-benzene dimer 2 through thermal and photoinduced electron transfer is studied using experimental and computational methods. The reaction of the radical cations formed by electron transfer is atleast 10(5) times faster than the thermal background reaction. It is demonstrated that the photoinduced electron transfer catalyzed reaction proceedsvia an electron transfer sensitized pathway and that the observed inverse secondary deuterium isotope effect of 0.91 +/- 0.02 on the reaction is due to the equilibrium isotope effect on the electron transfer step. The relevance of these findings on the mechanism of the electron transfer catalyzed [2 + 2] cycloreversion of the biologically important cis,syn-cyclobutane-thymine dimer is also discussed.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/12/20 alle ore 15:55:40