期刊
SYNTHESIS-STUTTGART
卷 54, 期 22, 页码 4971-4978出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1818-0576
关键词
benzynes; trifluoromethyl group; triptycenes; regioselective synthesis; cycloaddition; negative hyperconjugation
资金
- Japan Society for the Promotion of Science (JSPS) KAKENHI [JP18H02557, JP18H04418, JP18H04624, JP20H04780, JP20K21198, JP20K15283]
- Nagase Science Technology Foundation
- Asahi Glass Foundation
- Integrated Research Consortium on Chemical Sciences (IRCCS) Fusion Emergent Research Program
- National Science Foundation [1449440]
- Division Of Graduate Education
- Direct For Education and Human Resources [1449440] Funding Source: National Science Foundation
The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. High regioselectivity was achieved in the triple cycloaddition reaction of ynolates and the Diels-Alder reaction of anthranoxides with the benzyne, resulting in the synthesis of triptycenes with different trifluoromethyl substitution patterns.
The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels-Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne.
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