Experimental and theoretical study on the substitution reactions of aryl 2,4-dinitrophenyl carbonates with quinuclidines
2006; Elsevier BV; Volume: 62; Issue: 11 Linguagem: Inglês
10.1016/j.tet.2005.12.044
ISSN1464-5416
AutoresEnrique A. Castro, Paola R. Campodónico, Renato Contreras, Patricio Fuentealba, José G. Santos, J. Ramón Leis, Luis García‐Río, J.A. Sáez, Luís R. Domingo,
Tópico(s)Chemical Reactions and Mechanisms
ResumoThe reactions of quinuclidines with phenyl, 4-methylphenyl, and 4-chlorophenyl 2,4-dinitrophenyl carbonates are kinetically evaluated in aqueous solution. The Brønsted-type plots (log kN vs pKa of quinuclidinium ions) are linear. The magnitude of the slopes and validated theoretical scales of electrophilicity and nucleophilicity confirm the concerted nature of these reactions.
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