Generation and interception of bicyclo[3.2.1]oct-2-yne: an experimental and theoretical mechanistic study.
| Autor: | Anderson TE; Department of Chemistry, Colby College, Waterville, Maine 04901, USA. dmthamat@colby.edu., Chabuka BK; Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, USA., Alabugin IV; Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, USA., Thamattoor DM; Department of Chemistry, Colby College, Waterville, Maine 04901, USA. dmthamat@colby.edu., Phillips DL; Department of Chemistry, The University of Hong Kong, Pok Fu Lam, 999077, Hong Kong, S.A.R., P. R. China. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Oct 29. Date of Electronic Publication: 2024 Oct 29. |
| DOI: | 10.1039/d4cc03048f |
| Abstrakt: | Bicyclo[3.2.1]oct-2-yne was generated from the Fritsch-Buttenberg-Wiechell rearrangement of 2-norbornylidene carbene. The rearrangement preferentially involves migration of a tertiary carbon over a secondary carbon, a trend that contrasts with rearrangements of acyclic carbenes and which may be attributable to hyperconjugative effects promoted by the bridged structure of the carbene. |
| Databáze: | MEDLINE |
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