A Lewis Acid Stabilized Ketenimine in an Unusual Variant of the Electrophilic Aromatic Substitution.

ABSTRACT: Electrophilic aromatic substitution (EAS) can provide a straightforward approach to the efficient synthesis of functionalized complex aromatic molecules. In general, Lewis acids serve as a beneficial stimulus for the formation of a Wheland complex, the intermediate in the classical S_E Ar mechanism of EAS, which is responsible for H/E (E=electrophile) substitution under formal H⁺ elimination. Herein, we report an unusual variant of EAS, in which a complex molecule such as the tricyanomethane, HC(CN)₃ , is activated with a strong Lewis acid (B(C₆ F₅ )₃ ) to the point where it can finally be used in an EAS. However, the Lewis acid here causes the isomerization of the tricyanomethane to the ketenimine, HN=C=C(CN)₂ , w

SUBMITTER: Surkau J 

PROVIDER: S-EPMC10092272 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature