Sigmatropic rearrangement reactions are of prime interest in the construction of small complex molecules and find widespread application in drug discovery and natural product synthesis. Herein, we report on the application of aryl/aryl diazoalkanes in rhodium-catalyzed sigmatropic rearrangement reactions of allyl sulfides. Overall, a broad variety of different allyl sulfides and different aryl/aryl diazoalkanes were compatible and the desired products were obtained in high yield. Detailed studies on aryl/aryl diazoalkanes are still underrepresented in organic synthesis. Herein, we report on rhodium-catalyzed [2,3]-sigmatropic rearrangement reactions of such diazoalkanes to further broaden the applicability of aryl/aryl diazoalkanes for the construction of densely functionalized small molecules. [ABSTRACT FROM AUTHOR]