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The search for the gas-phase negative-ion pinacol rearrangement. 2—aryl rearrangements

✍ Scribed by Suresh Dua; Margaret J. Alexander; John H. Bowie

Book ID
102560331
Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
437 KB
Volume
28
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

Deprotonated phenyl ethylene glycols, on collisional activation, lose water by a negative ion pinacol rearrangement involving phenyl migration. For example, deprotonated benzpinacol undergoes the following reactions: Ph~2~C(OH)C(O^−^)Ph~2~ → [PhCOCPh~3~ – H]^−^ + H~2~O. It is proposed that this rearrangement proceeds from an eclipsed (or near eclipsed) conformer which is stabilized by the HO and O^−^ groups forming a strong intramolecular hydrogen bond.

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