| Radical Ion Probes. 9. The Chemistry of Radical Cations Derived from 9-Cyclopropylanthracene and 9-Bromo-10-cyclopropylanthracene. | |
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MedLine Citation:
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PMID: 11672053 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Reactions of radical cations generated from 9-cyclopropylanthracene (1) and 9-bromo-10-cyclopropylanthracene (2) in the presence of methanol have been investigated electrochemically. The major products arising from oxidation of both substrates are attributable to CH(3)OH attack at the aromatic ring (occurring at the radical cation stage for 2 and the dication stage for 1) rather than CH(3)OH-induced cyclopropane ring opening, which is estimated to be exothermic by 20 kcal/mol. Although ring-opened products are detected in some instances, these are found to arise from subsequent reaction of the primary oxidation products. These observations are consistent with a proposed product-like transition state for the nucleophile-induced ring opening of cyclopropylarene radical cations in which the positive charge is localized on the cyclopropyl group and nucleophile, and thus unable to derive stabilization from the aromatic ring. |
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Authors:
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Yonghui Wang; Karen H. McLean; J. M. Tanko |
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Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 63 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 1998 Feb |
Date Detail:
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Created Date: 2001-Oct-23 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: 628-635 Citation Subset: - |
Affiliation:
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Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061-0212. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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