Chemistry Letters, Vol.30, No.5, 448-449, 2001
Photochemical production of sugar-like interconvertible anomeric naphthopyranylhemiacetals from acenaphthylene and chloranil
Irradiation of acenaphthylene (ACN) and p-chloranil with > 420 nm light in 1,2-dichloroethane gives two interconvertible anomeric naphthopyranylhemiacetals in high yields (> 70%), whereas irradiation of ACN with other 1,3-benzoquinones does not afford this type of products. The above products will result from photochemical formation of an oxetane followed by its hydration. These products an stereoselectively converted into an identical naphthopyranylacetal in primary alcohols.