The photochemical reaction of ozone and n-butylferrocene has been studied using a combination of matrix isolation, infrared spectroscopy, and theoretical calculations. Experimental findings combined with theoretical calculations resulted in the observation of ethers formed when oxygen is inserted in either the butylcyclopentadienyl or cyclopentadienyl ring of n-butylferrocene. The formation of the ether is exothermic and results in ring opening to form an aldehyde.  Both the ether and aldehyde were only observed after the matrix was irradiated with red light (? = 600 nm). Notably the matrix turned from green to a red color after irradiation. Supporting data was obtained from 18O-labled ozone experiments.  In addition calculations at the B3LYP/6-311++G(d,2p) level provide further validation.  These results are comparable to those for the reaction of Ferrocene and ozone.

Ozone and n-butylferrocene: Fascinating photochemistry

248th National Meeting (2014)

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