CHED 399 |
| We have evidence that the thermolysis or photolysis of α-diazoacetylferrocene produces ferrocenylketene via the Wolff rearrangement. The ketene can be trapped by nucleophilic attack. Photolysis of α-diazoacetylferrocene in ethanol gave a product identified by mass spectroscopy to be ethyl ferrocenylacetate, which is consistent with the nucleophilic addition of ethanol to ferrocenylketene. Photolysis afforded only small amounts of ethoxyacetylferrocene, which is a significant product under thermal conditions. Photolysis of the diazoketone with propanol gave analogous results, but initial trials using diethylamine as the trapping agent have been unsuccessful. An effective method of purifying α-diazoacetylferrocene by column chromatography has also been developed. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |