Ring opening of 2,3-epoxy phenyl ketones upon reaction with nitric oxide

Epoxide rings of 2,3-epoxy phenyl ketones were cleaved by nitric oxide, affording regioselectively the C-3 ring-opened products, erythro-α-hydroxyl nitrates (2), in a highly syn-selective manner (isolated yield of the erythro products up to 91%). Products were identified by NMR, MS, and X-ray crystallography. The reaction is assumed to be initiated by NO2, unlike a nucleophilic attack.