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Rearrangement of 2-(4-Hydroxyalkyl)-1,3-dioxolanes to 2-Hydroxyethyl Alkanoic Esters by 1,5-Hydride Shift – An Unprecedented Intramolecular Redox Reaction

✍ Scribed by Karsten Krohn; Ulrich Flörke; Uwe Höfker; Marion Träubel

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 276 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199912)1999:12<3495::aid-ejoc3495>3.0.co;2-0

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✦ Synopsis

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 results of deuterium labeling experiments.

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