Leroux, FredericGaramszegi, LaszloSchlosser, Manfred2006-03-032006-03-032006-03-03200210.1016/S0022-1139(02)00151-3https://infoscience.epfl.ch/handle/20.500.14299/226992WOS:0001791522000151039Using in situ generated iodine fluoride as the reagent, bromine can be replaced by fluorine at carbocation-sustaining sites. Iodine fluoride or, being its operational equiv., the mixt. of N-iodosuccinimide and triethylamine tris(hydrogen fluoride) reacts with tertiary and benzylic bromoalkanes to afford the resp. fluoroalkanes in moderate-to-excellent yields. In contrast, primary bromoalkanes are virtually inert under identical conditions. Secondary bromoalkanes do not react either unless the heterolytically generated cationic intermediates benefit from non-classical resonance stabilization. [on SciFinder (R)]Fluorination (agents; prepn. of fluoroalkanes by chemoselectivestereoselective displacement of bromine at tertiarybenzylic or non-classical secondary sites using iodine fluoride); Alkyl bromides Role: RCT (Reactant)RACT (Reactant or reagent) (benzbromine displacement fluorine tertiary benzylic secondary alkane; bromoalkane bromine displacement fluorine tertiary benzylic secondary alkane; fluoroalkane prepn bromine displacement fluorine tertiary benzylic secondary alkane; benzyl bromide bromine dtext::journal::journal article::research article