We have studied the reactions of a variety of organic and inorganic acids with arynes generated by the hexadehydro-Diels–Alder (HDDA) reaction (e.g., 2 from 1). I will show our work on several such reactions, including the efficient trapping of arynes by carboxylic acids and an unusual acid-mediated C–H insertion process (cf. 2 to 3). I will present the results of kinetic and mechanistic experiments, as well as the insight they offer about the fundamental nature of aryne reactivity.

Exploring the reactivity of hexadehydro-Diels–Alder (HDDA)-generated benzynes with acids

249th National Meeting (2015)

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