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The Migratory Aptitude of the Ethoxycarbonyl Group in the Pinacol Rearrangement. Preliminary communication

✍ Scribed by Jacques Kagan; Dalmacio A. Agdeppa Jr.; S. P. Singh

Publisher
John Wiley and Sons
Year
1972
Tongue
German
Weight
192 KB
Volume
55
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 is comparable to that of ethyl, greater than that of methyl or hydrogen, but smaller than that of phenyl. Cyclization and fragmentation reactions were also observed.

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