期刊
TETRAHEDRON LETTERS
卷 52, 期 17, 页码 2051-2053出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.033
关键词
Perylene; Pyrolysis; Flow system; Rearomatization; Cyclodehydrogenation; Directed synthesis; Armchair nanotubes; Single-walled nanotubes
资金
- Department of Energy
- National Science Foundation
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0809494] Funding Source: National Science Foundation
Benzyne, generated in the gas phase by pyrolysis of phthalic anhydride, has been shown to undergo Diels-Alder cycloaddition to the bay region of perylene, a typical polycyclic aromatic hydrocarbon, under solvent-free conditions in a high temperature flow system. The initial cycloadduct spontaneously loses two hydrogen atoms, thereby rearomatizing to give naphtho[1,2,3,4-ghi]perylene. Analogous Diels-Alder cycloadditions of benzyne to bay regions on the rims of suitable cylindrical hydrocarbon templates, when followed by rearomatizations and thermal cyclodehydrogenations to join adjacent benzo groups, are proposed as key steps for a directed chemical synthesis of uniform diameter armchair carbon nanotubes. (C) 2010 Elsevier Ltd. All rights reserved.
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