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Among gas-phase dissociation reactions,double bond cleavage reaction appears to happen extremely rare,especially in the case of C=C double bond.In the dissociation reaction of protonated 2-benzylidenecyclopentanones in tandem mass spectrometry,the formation of benzyl cations was observed,resulting from the cleavage of C double bonds.A combined experimental and theoretical investigation on intramolecular hydrogen transfers was carried out to illustrate the mechanisms,which indicated that intramolecular proton-transport catalysis played a vital role in the reaction.