A new route to lactam precursors from cycloalkanes:: Direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide

Clean and selective: Nitrosation and oximation of cycloalkanes was achieved by treating them with tBuONO under Ar in the presente presence of a catalytic amount of N-hydroxyphthalimide (see scheme). The novel, clean nitrosation procedure uses halogen-free, relatively mild reaction conditions and results in good product selectivity (almost no organic byproducts) and high recovery of the catalyst.