A Facile Synthesis of 1,2-Divinylcycloalkanols and Their Behavior in the Oxy-Cope Rearrangement

Article abstract of DOI:10.1246/bcsj.53.2958

The reaction of 2-chlorocycloalkanones with vinylmagnesium chloride gives 1,2-divinylcycloalkanols.Divinylation proceeds via a rearrangement of initially formed 2-chloro-1-vinylcycloalkanols to 2-vinylcycloalkanones followed by further vinylation of 2-vinylcycloalkanones.Thermal sigmatropic rearrangement of 1,2-divinylcycloalkanols gives 5-cycloalken-1-ones in good yields.The influence of the size of rings on the reaction pathways is discussed.