Structures and Reactivities of Iminium Ions Derived from Substituted Cinnamaldehydes and Various Chiral Imidazolidin-4-ones

Autor:	Feng An, Shyeni Paul, Johannes Ammer, Peter Mayer, Herbert Mayr, Armin R. Ofial, Sami Lakhdar
Rok vydání:	2014
Předmět:	chemistry.chemical_compound Reaction rate constant chemistry Silylation Computational chemistry Organocatalysis Organic Chemistry Electrophile Ketene Iminium Tributylphosphine Free-energy relationship Photochemistry
Zdroj:	Asian Journal of Organic Chemistry. 3:550-555
ISSN:	2193-5807
DOI:	10.1002/ajoc.201402009
Popis:	A series of α,β-unsaturated iminium ions derived from substituted cinnamaldehydes and C2- and C5-substituted chiral imidazolidin-4-ones were isolated and characterized in solution and in the solid state. The kinetics of the reactions of the iminium ions with silyl ketene acetals were determined in dichloromethane at 20 °C. The resulting second-order rate constants were used to estimate the electrophilicity E of the iminium ions according to the linear free energy relationship log k2(20 °C)=sN(N+E). The kinetics for the reactions of two of the iminium ions with tributylphosphine were studied by laser flash spectroscopy and their second-order rate constants were found to agree within a factor of 2.2 with those calculated by using the linear free energy relationship above.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6c4534dbd1adffddbafa6b15af080677 https://doi.org/10.1002/ajoc.201402009 Zobrazit plný text záznamu Plný text