The Journal of organic chemistry

Aryl-Substituted Cyclopropyl Acetylenes as Sensitive Mechanistic Probes in the Gold-Catalyzed Hydration of Alkynes. Comparison to the Ag (I)-, Hg (II)-, and Fe (III)- …

G Velegraki, M Stratakis

Index: Velegraki, Georgia; Stratakis, Manolis Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8880 - 8884

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Citation Number: 10

Abstract

The gold-catalyzed hydration of 2-phenyl-or 2, 2-diphenylcyclopropyl acetylene, sensitive probes to trace the formation of vinyl carbocations, provides exclusively the corresponding cyclopropyl methyl ketones. On the other hand, in the Ag (I)-or Fe (III)-catalyzed hydration, a profound vinyl carbocationic character appears in the initially formed metal–alkyne complexes, as judged by the partial (Ag+) or exclusive (Fe3+) formation of allene-type ...

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