Migratory aptitudes of simple alkyl groups in the anionotropic rearrangement of quaternary chloromethyl borate species: A combined experimental and theoretical …

…, M Lombardo, A Neri, C Trombini

Index: Bottoni, Andrea; Lombardo, Marco; Neri, Andrea; Trombini, Claudio Journal of Organic Chemistry, 2003 , vol. 68, # 9 p. 3397 - 3405

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Citation Number: 20

Abstract

A combined experimental and theoretical investigation at the DFT and MP2 levels on the boron-to-carbon 1, 2-shift in “ate species”, coming from the quaternization of boranes (A) and boronate (B), is reported. To discuss the different migratory aptitudes of various alkyl groups, we have examined the migration of primary (R= Me, Et), secondary (R= i-Pr), and tertiary (R= t-Bu) alkyl groups. The effect of the counterion Li+ and of the solvent (polarized ...