Like the ortho-quinone methide (oQM), the aza analogue (aoQM) stands out as an exceptionally reactive intermediate owing to the sizeable rearomatization driving force. aoQMs have been postulated as short-lived intermediates in a number of pericyclic reactions and nucleophilic additions, though none have yet to be isolated. Computations reveal aoQMs are generally highly unstable intermediates, which are inaccessible at ambient temperatures compared to the easily accessible oxygen analogue. This discovery forces a reevaluation of the mechanisms of various room temperature aza-ortho-quinone-methide mediated reactions.

Do aza-ortho-quinone-methide mediated transformations involve aza-ortho-quinone-methides?

249th National Meeting (2015)

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