Abstract Strained nitroso Diels–Alder bicyclo [2.2. 1] or [2.2. 2] adducts functionalized with alkene side chains of diverse length undergo a ring-rearrangement metathesis process with external alkenes and Grubbs II or Hoveyda–Grubbs II ruthenium catalysts, under microwave irradiation or classical heating, to deliver cis-fused bicycles of various ring sizes, which contain a N [BOND] O bond. These scaffolds are of synthetic relevance for the generation ...