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Photochemical Formation of Aza-Quinone Methides by Dehydration and ESIPT of Aminoarenes

Aza-quinone methides (AQMs) are reactive intermediates that have attracted scientific interest owing to their application in organic synthesis.[1] AQMs can also be prepared in photochemical reactions, [2] which opens avenues to their potential applications in biological systems. However, contrary to the analogues phenolic intermediates quinone methides (QMs), [3] reports on AQM photochemical generations are scarce. It has been demonstrated that the antiaromatic character of excited states of phenolic derivatives drives the excited-state intramolecular proton transfer (ESIPT), which relieves the excess energy by forming less antiaromatic keto-tautomers.[4] We infer that analogous reasons initiate the photoreactions of phenols that deliver QMs such as photodehydration[5] and photodeamination.[6] Furthermore, we have recently extended the scope of investigation to photochemical reactivity of different anilines that undergo ESIPT to carbon atom, [7] or photodehydration. In both cases AQMs are formed as reactive intermediates, as shown for the ESIPT reaction of 1[7] or elimination of ROH from 2.

Excited state antiaromaticity ; Aza-quinone methides ; Excited state intramolecular proton transfer (ESIPT) ; Photodehydration

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