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A remarkable difference is observed in the rates of [3,3]-sigmatropic rearrangement of aryl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 1 and 2; the slower reactivity of the α-isomers is consistent with AM1 calculated transition state energetics of model systems.
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Journal of the Chemical Society, Perkin Transactions 2
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