FUNCTIONALIZATION OF UNACTIVATED CARBON INVOLVING PHOTOCHEMICAL INTRAMOLECULAR REARRANGEMENT OF NITRO GROUP ATTACHED TO TETRAHEDRAL CARBON TO NITROSOOXY GROUP
Photolysis of both 6β-nitrocholest-4-ene and 4β-nitrocholest-6-ene gave a mixture of (E)-19-hydroxyiminocholest-4-en-6β-ol and (E)-19-hydroxyiminocholest-5-en-4β-ol; this mixture arose in both cases from a photochemical nitro-nitrosooxy rearrangement followed by the Barton reaction. The structures of the products were established by their synthesis.