A novel synthetic protocol that uses halogenation reagents (NBS, NIS and selectfluor) to initiate intramolecular ring-opening reactions of diarylvinylidenecyclopropanes (VDCPs) connected to alcohol-bearing chains has been developed. The approach provides a variety of halogenated tetrahydropyran derivatives in moderate to good yields under mild conditions. Plausible reaction mechanisms are proposed on the basis of previous literature and the substrate scope has been carefully examined.
Yuan W,Shi M. Halogenation Reagents Initiating Ring Opening of Vinylidenecyclopropanes: Easy Access to Halogenated Tetrahydropyrans[J]. Synlett,2011(7):995-999.
