Cleavage of (3-chloro-2-methylenecycloalkyl)palladium Chloride Dimers: Formation of Olefins and α-methoxyolefins
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 carbocydic 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(0) generates a new π-allyl complex which affords the olefin product upon subsequent cleavage.
Donaldson, William, "Cleavage of (3-chloro-2-methylenecycloalkyl)palladium Chloride Dimers: Formation of Olefins and α-methoxyolefins" (1987). Chemistry Faculty Research and Publications. 864.