Abstract
A mild and convenient reaction of amine–boranes and oxalic acid to bi‐ or tricyclic spiroborate compounds is presented. The substitution position (on the N or B atom) of amine–boranes plays an important role on the divergence of reaction pathways: ammonia–borane (NH3·BH3, AB) or N‐substituted amine–boranes NHnMe3–n·BH3 (n = 0, 1, 2) give bicyclic spiroborate compounds 1a–d, whereas B‐substituted amine–borane NH3·BH2Me leads to tricyclic spiroborate compound 3. Fortunately, acyloxyboranes were detected as important intermediates by NMR spectroscopy in the reaction of ammonia–borane and oxalic acid, uncovering a stepwise dehydrogenation pathway.
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