期刊
TETRAHEDRON
卷 66, 期 40, 页码 7933-7938出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.07.046
关键词
Polycyclic aromatic hydrocarbons; Diels-Alder reaction; Hetero-Diels-Alder reaction
资金
- National Science Foundation [CHE-0936862]
- Petroleum Research Fund [45801-AC4]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [936862] Funding Source: National Science Foundation
The thermal reaction of phencyclone (2) with a 1:1 mixture of 1,8-pyrenequinone (4) and 1,6-pyrenequinone (5) yields 21 adducts only of compounds 2 and 4. The observed polycyclic aromatic hydrocarbon 8 is formed via double Diels-Alder addition of 2 to 4, and the polycyclic ketone 9 arises from a combination of Diels-Alder and hetero-Diels-Alder reactions of 2 and 4. In contrast, Lewis acid-catalyzed reactions of 2, 4, and 5 give 2:1 adducts only of 2 and 5. The chief product, polycyclic diketone 10, is derived from a double hetero-Diels-Alder addition of 2 to 5. X-ray analysis of compound 8 shows it to be an exceptionally large polycyclic aromatic arch, and the X-ray structure of 10 reveals it to be a chiral molecular tweezer. (C) 2010 Elsevier Ltd. All rights reserved.
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