Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 5, Pages 1298-1302Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609111
Keywords
aryne; directing effect; hyperconjugation; triptycene; ynolate
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Funding
- JSPS KAKENHI [JP16H01157, JP26293004]
- Science and Technology Research Promotion Program for Agriculture, forestry, fisheries and food industry
- Asahi Glass Foundation
- Cooperative Research Program of the Network Joint Research Center for Materials and Devices
- National Science Foundation [CHE-1152491]
- NSF XSEDE [TG-CHE160006]
- IBM
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1465142] Funding Source: National Science Foundation
- Grants-in-Aid for Scientific Research [26293004, 16H01157, 17K15430] Funding Source: KAKEN
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We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C-3-symmetrical triptycenes hold promise in the design of functional materials.
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