Intramolecular anodic carbon-carbon bond-forming reactions of oxidized phenol intermediates leading to spirodienones. Structural effects on reactivity and evidence for a phenoxonium ion intermediate

Autor:	John S. Swenton, Gary W. Morrow, Y. Chen, Michael Lester Kerns, Kenneth Carpenter
Rok vydání:	1993
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Addition reaction Reaction mechanism chemistry Carbon–carbon bond Intramolecular force Yield (chemistry) Organic Chemistry Phenol Reactivity (chemistry) Methanol Photochemistry
Zdroj:	The Journal of Organic Chemistry. 58:3308-3316
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00064a017
Popis:	Anodic oxidation of 4-phenylphenol in methanol leads to 4-methoxy-4-phenylcyclohexa-2,5-dienones whereas anodic oxidation of 4-(2-alkenylphenyl)-phenols leads to spirocyclic 2,5-cyclohexadienones in competition with methanol addition to the 4-position. Using 4-phenylphenol and -1-(2-propenylphenyl)phenol as model systems, the optimum conditions for solvent addition versus carbon-carbon bond formation have been studied. The yield of the anodic cyclization reaction shows a dramatic dependence on olefin structure. Whereas 4-(2-propenylphenyl)phenol gives the spirocyclic 2,5-cyclohexadienone in high yield, 4-(2-vinylphenyl)phenol affords the analogous product in only 16% yield
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d03ee6598a6e81b320f880479e0a0c9f https://doi.org/10.1021/jo00064a017 Zobrazit plný text záznamu