| DOI | Resolve DOI: https://doi.org/10.1021/jo0009200 |
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| Author | Search for: Mladenova, Gabriela; Search for: Chen, Lie1; Search for: Rodriquez, Chris F.; Search for: Siu, K. W. Michael; Search for: Johnston, Linda J.1; Search for: Hopkinson, Allan C.; Search for: Lee-Ruff, Edward |
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| Affiliation | - National Research Council of Canada. NRC Steacie Institute for Molecular Sciences
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| Format | Text, Article |
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| Abstract | The substituted fluorenyl cation, 9-(diphenylmethyl)fluoren-9-yl cation (4), is formed under stable ion conditions (low temperature/strong acid) from its corresponding alcohol 3. This ion is transformed to a substituted diphenyl methyl cation 8 at ambient temperature via an apparent 1,2-hydrogen shift. Irradiation of 9-(diphenylmethyl)fluoren-9-ol in methanol gives products derived from the corresponding cation along with radical-derived products from C-C and C-O homolysis processes. The laser flash photolysis of this alcohol gave a transient corresponding to cation 4. All of the photoproducts are derived from cation 4 or radical pathways. High level MO calculations point to a high barrier (23.8 kcal mol-1) for the 1,2-hydride shift. This barrier is the consequence of the minimum energy conformation of this fluorenyl cation which is less than ideal for the periplanar geometry necessary for this process. |
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| Publication date | 2001-02-27 |
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| In | |
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| Language | English |
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| NPARC number | 12328577 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | b5538f3c-b759-4e35-9ac0-ea315c32247e |
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| Record created | 2009-09-10 |
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| Record modified | 2020-03-27 |
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