Selective Oxidation of Belt[4]arene[4]tropilidene and Its Application to Construct Hydrocarbon Belts of Truncated Cone Structure with Expand Cavity
- 2 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7259-7263
- https://doi.org/10.1021/acs.orglett.1c02643
Abstract
Despite their unique structures, tantalizing properties, and potential applications in carbon nanoscience and technology, the synthesis and functionalization of zigzag hydrocarbon nanobelts have remained largely unexplored until recently. Reported herein is the selective transformations of belt[4]arene[4]tropilidenes and their application in the construction of novel belts. The oxidation of belt[4]arene[4]tropilidene with benzeneseleninic anhydride under controlled conditions selectively afforded mono- to tetrakis(α-diketone)-functionalized belt intermediates. A subsequent condensation reaction with 1,2-phenylenediacetonitrile and 1,2-phenylenediamine produced a diversity of unprecedented belts with various macrocyclic cavities.Keywords
Funding Information
- Tsinghua Initiative Scientific Research Program (2019Z07L01004)
- National Natural Science Foundation of China (21732004, 21821001, 22050005)
This publication has 27 references indexed in Scilit:
- Exploring a Route to Cyclic Acenes by On‐Surface SynthesisAngewandte Chemie, 2019
- Synthesis of Armchair and Chiral Carbon NanobeltsChem, 2019
- Synthesis and Size-Dependent Properties of [12], [16], and [24]Carbon NanobeltsJournal of the American Chemical Society, 2018
- Rigid tetraarylene-bridged cavitands from reduced-symmetry resorcin[4]arene derivativesChemical Communications, 2018
- Synthesis of a carbon nanobeltScience, 2017
- Aromatic Saddles Containing Two HeptagonsJournal of the American Chemical Society, 2015
- Facile and highly chemoselective synthesis of benzil derivatives via oxidation of stilbenes in an I2–H2O systemRSC Advances, 2013
- Ruthenium-Catalyzed Oxidation of Alkenes at Room Temperature: A Practical and Concise Approach to α-DiketonesOrganic Letters, 2011
- Synthesis of [6.8]3Cyclacene: Conjugated Belt and Model for an Unusual Type of Carbon NanotubeJournal of the American Chemical Society, 2008
- Doubly Ortho-Linked Quinoxaline/Diphenylfluorene Hybrids as Bipolar, Fluorescent Chameleons for Optoelectronic ApplicationsJournal of the American Chemical Society, 2006