Automerization of an Enediyne via a Symmetrical <i>p</i>-Benzyne Diradical Intermediate
Automerization is defined as a rearrangement reaction that yields a degenerate form of the starting material. We now report that cyclohexeno[3,4]cyclodeca-1,5-diyne-3-ene rearranges to its automer, via a <i>D</i><sub>2h</sub>-symmetric <i>p</i>-benzyne intermediate. The NMR evidence is that when the enediyne is heated to 75 °C in DMSO with either LiI or NaNO<sub>3</sub> as possible nucleophile, the enediyne is consumed only in the presence of LiI, whereas it remains "unchanged" in the presence of NaNO<sub>3</sub>.
Authors
- Đình Phiên Trần (ORCID: https://orcid.org/0000-0002-6337-8612)
- Charles L. Perrin (ORCID: https://orcid.org/0000-0001-5732-5330)
Institutions
- University of California San Diego (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-04
- DOI
- https://doi.org/10.1021/acs.joc.4c03144
- Citations
- 1
- Primary Topic
- Cyclization and Aryne Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- University of California, San Diego