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All calculations were performed with AMPAC 8.16. Semichem, Inc., PO Box 1649, Shawnee, KS 66222, USA
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3-catalyzed reaction.
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33748321364
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+) is indeed exothermic, but we were not able to find an original reaction path leading to tetrahydrofuran 2d with a comparable or even lower activation energy than that found starting from the O complex (Table 3, entries 7 and 9). Indeed, if the reaction is to proceed, the chelate must he cleaved, and due to the relative strengths of complexation (π complexation vs O complexation), the Lewis acid remains on the oxygen atom. From these results, we propose to explain the NMR chemical shifts observed for the ethylenic carbon atoms either as resulting from the formation of this chelate B or from the C=C complex C. Both complexes can not lead to the product of the reaction, but since their formation is reversible, they can exist and therefore be observed by spectroscopy.
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