Epoxide Formation by Ring Closure of the Cinnamyloxy Radical

Autor:	Jérôme Amaudrut, Olaf Wiest
Rok vydání:	2000
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Radical Organic Chemistry Photodissociation Epoxide Physical and Theoretical Chemistry Alkoxy radical Ring (chemistry) Biochemistry Medicinal chemistry Alkyl
Zdroj:	Organic Letters. 2:1251-1254
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol005749t
Popis:	[formula: see text] 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 approximately 5 kcal/mol more stable than the open one.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2324b3a113cec6418e73309776eed29a https://doi.org/10.1021/ol005749t Zobrazit plný text záznamu