Acid-Responsive Dissociation of Ferrocene Compounds: Diels–Alder Diene Equivalents for Selective Preparation of [60]Fullerene-Fused Bicyclo[2.2.1]hept-5-enes

Herein, an unprecedented transformation of [60]­fullerene with ferrocene compounds giving access to various [60]­fullerene-fused bicyclo[2.2.1]­hept-5-enes is presented. In the presence of an acid, ferrocene compounds undergo an unusual dissociation process and serve as Diels–Alder diene equivalents...

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Veröffentlicht in:Journal of organic chemistry 2022-03, Vol.87 (5), p.3104-3113
Hauptverfasser: Liu, Tong-Xin, Wu, Han, Ma, Nana, Zhang, Chuanjie, Zhang, Pengling, Ma, Jinliang, Zhang, Guisheng
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, an unprecedented transformation of [60]­fullerene with ferrocene compounds giving access to various [60]­fullerene-fused bicyclo[2.2.1]­hept-5-enes is presented. In the presence of an acid, ferrocene compounds undergo an unusual dissociation process and serve as Diels–Alder diene equivalents to react with [60]­fullerene for the selective construction of a class of novel fullerene-fused bridged carbocyclic derivatives. The reaction is easy to perform and has a wide substrate scope as well as excellent functional group compatibility, representing a new application of ferrocene compounds in synthetic chemistry.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02875