Automerization of an Enediyne via a Symmetrical <i>p</i>-Benzyne Diradical Intermediate.

ABSTRACT: 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 NaNO₃ as possible nucleophile, the enediyne is consumed only in the presence of LiI, whereas it remains "unchanged" in the presence of NaNO₃.

SUBMITTER: Perrin CL 

PROVIDER: S-EPMC11915363 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature