Work

Automerization of an Enediyne via a Symmetrical p-Benzyne Diradical Intermediate

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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 D 2h -symmetric p -benzyne intermediate. The NMR evidence is that when the enediyne is heated to 75 °C in DMSO with either LiI or NaNO 3 as possible nucleophile, the enediyne is consumed only in the presence of LiI, whereas it remains “unchanged” in the presence of NaNO 3 .

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c03144

Authors: Charles L. Perrin, Denise H. Tran

Institution: University of California San Diego

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: University of California, San Diego