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Diels–Alder reactions and electrophilic substitutions with atypical regioselectivity enable functionalization of terminal rings of anthracene

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Huynh, Vinh Ngoc ; Leitner, Michael ; Bhattacharyya, Aditya ; Uhlstein, Lisa ; Kreitmeier, Peter ; Sakrausky, Patrick ; Rehbein, Julia ; Reiser, Oliver
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Date of publication of this fulltext: 23 Feb 2021 12:36


Reversing the regioselectivity of the renowned Diels-Alder reaction by overriding the usual thermodynamic and kinetic governing factors has always been a formidable challenge to synthetic organic chemists. Anthracenes are well-known to undergo [4 + 2]-cycloadditions with dienophiles at their 9,10-positions (central ring) over 1,4-positions (terminal ring) guided by the relative aromatic ...


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