Experimental and Theoretical Study of the 2-Alkoxyethylidene Rearrangement

KS Graves, DM Thamattoor…

Index: Graves, Kimberly S.; Thamattoor, Dasan M.; Rablen, Paul R. Journal of Organic Chemistry, 2011 ,  vol. 76,  # 6  p. 1584 - 1591

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Citation Number: 13

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 ...