The gas phase reaction of boron monoxide radical and allene was investigated computationally through <i>ab initio</i> electronic structure calculations and experimentally using the crossed molecular beam technique. The reaction proceeds through the formation of a van der Waals complex isomerized by the addition of the boron monoxide radical to the terminal carbon atom of allene. The chemically active intermediate decomposes via Hydrogen elimination at the boronyl carbon to synthesize boronylallene in an exoergic reaction. RRKM statisitical calculations suggest minor reaction pathways leading to a 1-propynyloxoborane and 3-propynyloxoborane product. The boronylallene reaction was compared with the cyanoallene and boronyl–methylacetylene reactions to probe differences and similarities of the isoelectronic systems. We present a novel gas phase synthesis of the elusive boronylallene, which has proven difficult to isolate in the condensed phase, and demonstrate that the crossed molecular beams technique is useful method for synthesis of highly reactive organyloxoboranes.

Computational and crossed molecular beam study in the synthesis of boronylallene

249th National Meeting (2015)

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