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A New Zincate-Mediated Rearrangement Reaction of 2-(1-Hydroxyalkyl)-1-alkylcyclopropanol

✍ Scribed by Kenichi Nomura; Seijiro Matsubara

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
259 KB
Volume
16
Category
Article
ISSN
0947-6539

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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