Aromatic C–C Bond Cleavage in a Curved π-System of Aminocorannulene

Abstract

We report a metal- and oxidant-free aromatic C–C bond cleavage in the curved corannulene skeleton. Reaction of 1-aminocorannulene with hydrazonyl chloride generates an amidrazone intermediate that undergoes facile intramolecular proton migrations and ring annulation to give a 1,2,4-triazole derivative of planar benzo[ghi]fluoranthene, in which the release of strain associated with the curved π-surface and the formation of an aromatic triazole moiety are the driving forces. This report provides new insights into the aromatic C–C bond cleavage.

Unlocking mild-condition benzene ring contraction using nonheme diiron N-oxygenase

“…1B). 6–15 Therefore, mild-condition enzymatic contraction of the benzene ring is of great importance and yet challenging. In this study, we report an aqueous-phase phloroglucinol benzene RCT facilitated by an engineered non-heme diiron N -oxygenase, AzoC-III (Fig.…”