Experimental and theoretical study of the 2-alkoxyethylidene rearrangement |
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Authors: | Graves Kimberly S Thamattoor Dasan M Rablen Paul R |
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Affiliation: | Department of Chemistry, Colby College, Waterville, Maine 04901, USA. |
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Abstract: | The rearrangement of 2-ethoxyethylidene, generated photochemically from a nonnitrogenous precursor, leads to ethyl vinyl ether. Although this product could result, in principle, from a 1,2-hydrogen shift and/or a 1,2-ethoxy shift in the carbene, a deuterium labeling study indicates an essentially exclusive preference for hydrogen migration. The experimental results are in agreement with CCSD and W1BD calculations for the simpler 2-methoxyethylidene system that show a prohibitively large barrier for the methoxy shift and a negligible barrier for the hydride shift. |
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