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Intrinsic migration aptitudes of alkyl groups in a pinacol rearrangement

✍ Scribed by Eckehardt Wistuba; Christoph Rüchardt


Book ID
104234399
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
201 KB
Volume
22
Category
Article
ISSN
0040-4039

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## Abstract The migratory aptitude of the ethoxycarbonyl group in the pinacol rearrangement was deduced from the structure of the products observed after treatment of 2‐substituted 2,3‐dihydroxy‐3‐phenylbutyrates with fluorosulfonic acid at 0° for 3 minutes. The migratory aptitude of ethoxycarbonyl

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DFT calculations at the Becke3LYP/6-31G\* level were employed to demonstrate that the pinacol rearrangement of ethylene glycol and the 1,1-dimethyl and 1,1,2-trimethyl analogs undergo pinacol rearrangements by a concerted hydrogen-bridged transition structure. No evidence for a bridged intermediate