Beilstein J. Org. Chem.2014,10, 2531–2538, doi:10.3762/bjoc.10.264
of the superoxideion leading to the synthesis of tetrachloroaryl/vinyl-substituted nortricyclenes through its dual mode of action has been reported. KO2 was found to be superior and the only reagent to perform this kind of reaction over other conventional bases. Addition of the antioxidant BHT (2,6
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Keywords: BHT; dehydrohalogenation/rearrangement; Friedel–Crafts acylation; methylenenortricyclene; superoxideion; Introduction
The chemistry of the superoxideion (O2−·) has been a subject of growing interest because of its presence in all aerobic organisms as a respiratory intermediate [1][2][3][4][5
][6]. The study of the reactivity of the superoxideion with organic substrates can facilitate understanding its role in metabolic processes [5]. Despite its biochemical importance, in organic synthesis, the superoxideion has mainly been used for electron transfer reactions [7][8][9], oxidation [10
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Graphical Abstract
Scheme 1:
Synthesis of Nortricyclenes from Norbornenes.