In recent years the hexadehydro-Diels–Alder (HDDA) reaction (e.g., cf. 1 to 2) has revealed previously unknown reactivity of benzynes (2). The ability to generate benzyne under mild, neutral reaction conditions free of any byproducts often allows for more thorough investigation of the mechanism of the trapping event. The addition of tertiary amines to benzynes is thought to pass through zwiterionic intermediates like 3. I will present findings on the determination of the mechanistic pathway for tertiary amine addition to HDDA-generated benzynes to give products like 4. I will also show novel applications of tertiary amine additions based on this new mechanistic understanding.

Mechanistic studies and applications of tertiary amine trapping of HDDA-generated benzynes

249th National Meeting (2015)

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