Biologically potent and synthetically significant 1,2-dihydronaphthalene derivatives have gained considerable attention due to their wide applications in industrial as well as in medicinal fields also. A mild and efficient metal-free protocol via the rearrangement of cyclopropylcarbinols has been reported to construct these 1,2-dihydronaphthalene skeletons utilizing cyclopropane ring as the scaffold. We obtained conjugated dienes and, in some cases, homoallylic chlorides as major products in good to excellent yields. They have no literature precedence till date. The fate of this rearrangement depends on the substituent patterns of the cyclopropane bearing aryl moiety. Besides the synthetic studies, to get deep insight into the electronic transitions, time dependent DFT studies have also been performed. © 2022 Wiley-VCH GmbH.