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Titolo:
Epoxide formation by ring closure of the cinnamyloxy radical
Autore:
Amaudrut, J; Wiest, O;
Indirizzi:
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:
ORGANIC LETTERS
fascicolo: 9, volume: 2, anno: 2000,
pagine: 1251 - 1254
SICI:
1523-7060(20000504)2:9<1251:EFBRCO>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
OXIRANYLCARBINYL RADICALS; FRAGMENTATION CHEMISTRY; ALPHA-IODOEPOXIDES; ALLYLOXY RADICALS; ALKYL RADICALS; RATE CONSTANTS; OXIRANYLMETHYL; REARRANGEMENT; CYCLOPENTANOLS; CARBOCYCLES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
40
Recensione:
Indirizzi per estratti:
Indirizzo: Wiest, O Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA Univ Notre Dame Notre Dame IN USA 46556 Notre Dame, IN 46556 USA
Citazione:
J. Amaudrut e O. Wiest, "Epoxide formation by ring closure of the cinnamyloxy radical", ORG LETT, 2(9), 2000, pp. 1251-1254

Abstract

The cinnamyloxy and oxiranyl benzyl radicals were generated by photolysis of alkyl 4-nitrobenzenesulfenates. The yet unprecedented epoxide ring formation from a primary alkoxy radical was observed. Experimental evidence supports the fact that the mode of ring opening of the oxiranyl carbinyl radical system is thermodynamically driven. B3LYP/6-31G* calculations indicate that the closed form of the radical is similar to 5 kcal/mol more stable thanthe open one.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/12/20 alle ore 15:39:01