Wikipedia
Perchlorylbenzene
Perchlorylbenzene (CHClO, PhClO, systematic name: phenyltrioxo-λ-chlorane) is an aromatic compound prepared by direct electrophilic perchlorylation of benzene using perchloryl fluoride and aluminum trichloride:
Ph-H + F-ClO + AlCl → Ph-ClO + HCl + AlClF (93% yield, based on AlCl)
The compound is described as a somewhat shock-sensitive oily liquid (b.p. 232 °C @ 760 mmHg, 78 °C @ 2 mmHg). It exhibits low chemical reactivity and is inert towards acidic (HCl (aq.)) or reducing (LiAlH, H/Pd) conditions. However, it undergoes hydrolysis upon reflux in aqueous KOH:
Ph-ClO + KOH → Ph-OH + KClO
It and its derivatives have been investigated as novel energetic materials analogous to nitro compounds.