Aprotic solvents are usually preferred for the SN2 reactions, because nucleophilicity and hence SN2 reactivity are severely retarded by the influence of the partial positive charge of protic solvents. In this work, we introduce a remarkable effect of using tertiary alcohols as a reaction medium for nucleophilic fluorination with alkali metal fluorides. In this novel synthetic method, the nonpolar protic tert-alcohol enhances the nucleophilicity of the ...
[McDonald, Chriss E.; Ramsey, Jeremy R.; Sampsell, David G.; Anderson, Laura A.; Krebs, Jordan E.; Smith, Samantha N. Tetrahedron, 2013 , vol. 69, # 14 p. 2947 - 2953]
