Bicycloannulation with nitroethene and 1-nitropropene. A one-step synthesis of tricyclenone
Abstract
Tricyclo [3.2.1.02,7]octan-6-ones and tricyclo-[2.2.1.02,6]heptan-3-ones are formed in one step from αβ-cyclohexenones and αβ-cyclopentenones, respectively, by treatment of their α′enolates with nitroethene and 1-nitropropene in tetrahydrofuran and then refluxing the resulting solution with added hexamethylphosphoric trimide.