Abstract

7,7-Dimethyl-2-methylenenorbornan-1-ol, a strained bicyclic 1-alkenyl cyclopentanol, undergoes Wagner–Meerwein rearrangement to fenchone under treatment with a catalytic amount of PdCl 2(PPh 3) 2 in refluxing N-methylpyrrolidin-2-one. The described reaction constitutes the first example of the palladium(II)-catalyzed ring expansion of 1-alkenyl cyclopentanols to the corresponding cyclohexanones.

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