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An Interrupted [4+3] Cycloaddition Reaction: A Hydride Shift (Ene Reaction) Intervenes

✍ Scribed by Michael Harmata; Chaofeng Huang; Parham Rooshenas; Peter R. Schreiner


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
414 KB
Volume
47
Category
Article
ISSN
0044-8249

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2-(4-Hydroxyalkyl)-1,3-dioxolanes (3a/3b, 5-7) undergo an via the benzylic carbenium ion B and the 1,3-dioxolan-2ylium cation C, is supported by the stereochemistry of the acid-catalyzed rearrangement to give 2-hydroxyethyl alkanoic esters 8-11. The postulated mechanism, proceeding reaction and the