Borate anions are potential components of electron-donor groups for donor-sigma-acceptor molecules. As a model, we have prepared N-benzyl and N-methyl pyridinium zwitterions with a 4-borate group. The borate is esterified with the triol 2-(hydroxymethyl)-2-methylpropane-1,3-diol. Alkylation of the pyridineborate anion was more successful than alkylation prior to closing of the borate. Pyridinium formation resulted in electron withdrawal from, and borate formation in electron release to the aromatic ring, as evidenced by nmr. Cyclic voltammetry of the compounds will be discussed. 

4-Methyl 1-(<i>N</i>-alkylpyridin-1-ium-4-yl)-2,6,7-trioxa-1-boranuidabicyclo[2.2.2]octane

245th National Meeting (2013)

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4-Methyl 1-(N-alkylpyridin-1-ium-4-yl)-2,6,7-trioxa-1-boranuidabicyclo[2.2.2]octane