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Creators/Authors contains: "Robichaud, Hannah M."

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  1. ; ; ; ; ; (, Organic & Biomolecular Chemistry)
    The first aromatic Claisen rearrangement of a 1,2-azaborine is described along with a quantitative kinetic comparison of the reaction of the azaborine with its direct all-carbon analogue. The azaborine A rearranged in a clean, regioselective fashion and reacted faster than the all-carbon substrate B at all temperatures from 140–180 °C. Activation free energies were extracted from observed first-order rate constants (A: Δ G ‡298K = 32.7 kcal mol −1 ; B: Δ G ‡298K = 34.8 kcal mol −1 ) corresponding to a twenty fold faster rate for A at observed reaction temperatures. DFT calculations show that the rearrangement proceeds via a concerted six-membered transition state and that the electronic structure of the BN and CC rings is mostly responsible for the observed regioselectivity and relative reactivity. 
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