In conclusion, we have presented in this work a detailed study of the reactivity of biradicals generated from the direct photoexcitation of carbonyl cyclopropanes. Depending on the substrate structure, intramolecular photoisomerization processes were favored or [3+2] annulations could be developed. Quantum chemical computations confirmed that 1,3 biradicals are viable key intermediates. By taking advantage of this common intermediate, a unified reductive strategy for the ring-opening of carbonyl cyclopropanes was achieved using diphenyl disulfide as a HAT reagent. These transformations pave the way for the development of new homologation strategies resulting in formal CH2 insertion onto the , c-C bond of unsaturated carbonyl compounds, extending the current toolbox 24 for the "skeletal editing" of organic compounds.