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Article: Dodecamethoxy- and hexaoxotricyclobutabenzene: Synthesis and characterization
Title | Dodecamethoxy- and hexaoxotricyclobutabenzene: Synthesis and characterization |
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Authors | |
Issue Date | 2006 |
Citation | Journal of the American Chemical Society, 2006, v. 128, n. 31, p. 10032-10033 How to Cite? |
Abstract | We report herein the syntheses of dodecamethoxytricyclobutabenzene (TCBB) 1 and hexaoxo-TCBB 2, a class of molecules with structural and theoretical interest. The preparation is based on the 3-fold [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where the selectively protected 2-iodophloroglucinol derivative served as a synthetic equivalent of benztriyne I, allowing rapid and regioselective annulation of fully functionalized four-membered rings. Structural study on the former compound showed that the C-C bond lengths in the central benzene ring were essentially the same. Copyright © 2006 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/341085 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Hamura, Toshiyuki | - |
dc.contributor.author | Ibusuki, Yousuke | - |
dc.contributor.author | Uekusa, Hidehiro | - |
dc.contributor.author | Matsumoto, Takashi | - |
dc.contributor.author | Siegel, Jay S. | - |
dc.contributor.author | Baldridge, Kim K. | - |
dc.contributor.author | Suzuki, Keisuke | - |
dc.date.accessioned | 2024-03-13T08:40:02Z | - |
dc.date.available | 2024-03-13T08:40:02Z | - |
dc.date.issued | 2006 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2006, v. 128, n. 31, p. 10032-10033 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341085 | - |
dc.description.abstract | We report herein the syntheses of dodecamethoxytricyclobutabenzene (TCBB) 1 and hexaoxo-TCBB 2, a class of molecules with structural and theoretical interest. The preparation is based on the 3-fold [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where the selectively protected 2-iodophloroglucinol derivative served as a synthetic equivalent of benztriyne I, allowing rapid and regioselective annulation of fully functionalized four-membered rings. Structural study on the former compound showed that the C-C bond lengths in the central benzene ring were essentially the same. Copyright © 2006 American Chemical Society. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Dodecamethoxy- and hexaoxotricyclobutabenzene: Synthesis and characterization | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja064063e | - |
dc.identifier.scopus | eid_2-s2.0-33746885487 | - |
dc.identifier.volume | 128 | - |
dc.identifier.issue | 31 | - |
dc.identifier.spage | 10032 | - |
dc.identifier.epage | 10033 | - |
dc.identifier.isi | WOS:000239454800025 | - |