CLEAVAGE OF (3-CHLORO-2-METHYLENECYCLOALKYL)PALLADIUM CHLORIDE DIMERS: FORMATION OF OLEFINS AND α-METHOXYOLEFINS

Article abstract of DOI:10.1016/S0040-4020(01)86828-9

The cleavage of the title compounds (7) in methanolic potassium hydroxide gives mixtures of olefins and α-methoxyolefins in good yields.The ratio of the products is dependent on the size of the carbocyclic ring.The mechanism proposed involves cleavage of 7 to the corresponding allylic chloride (8).Solvolysis of the chloride gives the α-methoxyolefin.Alternatively, oxidative addition of 8 to Pd(O) generates a new ?-allyl complex which affords the olefin product upon subsequent cleavage.