Experimental and theoretical studies of acid-catalyzed oxygen-18 exchange rates of conformationally rigid ketones. Is the antiperiplanar effect important?

Autor:	K. N. Houk, Fanzuo Kong, Yun Dong Wu, Robert R. Fraser, Maria Stanciulescu
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Acid catalysis Addition reaction Oxygen-18 Ketone Chemistry Stereochemistry Acid catalyzed Organic Chemistry Alkane stereochemistry Molecule Catalysis
Zdroj:	The Journal of Organic Chemistry. 58:4431-4440
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00068a044
Popis:	The relative rates for the acid-catalyzed addition of H 2 18 O to the carbonyl group of the conformationally fixed bridged biaryl ketone, 1, and several derivatives bearing methyl, chloro, and methoxy substituents in axial-like and equatorial-like orientations have been measured. The effects of axial- versus diaxiallike methyl and chloro substituents produce rate decreases which are consistentwith the antiperiplanar (hyperconjugative) interaction proposed by Cieplak; however, the negligible influence of a methoxy group when antiperiplanar is not consistent
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::19085046903a308cca5ce4a4dbe4b16d https://doi.org/10.1021/jo00068a044 Zobrazit plný text záznamu