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Title: The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes
Bis(azoliums) are readily available in one step from cyclic (alkyl)(amino)carbenes and bis(acyl chlorides). A two-electron reduction of the bis(azolium), featuring a gem -(dimethyl)malonoyl spacer, leads to the corresponding transient diradical, which undergoes an intramolecular cyclization. The latter can be re-oxidized at a higher potential to yield back the bis(azolium). The redox bistability of this simple organic molecular system is linked to the formation of a weak C–O bond (27 kcal mol −1 ). Both redox forms can be isolated and stored for months without evidence of decay.  more » « less
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Author(s) / Creator(s):
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Date Published:
Journal Name:
Organic Chemistry Frontiers
Page Range / eLocation ID:
2073 to 2078
Medium: X
Sponsoring Org:
National Science Foundation
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