The Reactivity of Potassium Carbanions with Epoxides

Abstract

Cyclohexene oxide reacted with n-butylpotassium unexpectedly to produce 2-butylcyclohexanone in a 10% isolated yield of its semicarbazone derivative. Based on previous literature, a three-part mechanism is proposed that implies that a yield greater than 33% is not possible.

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GRAPHICAL ABSTRACT

Keywords:

• 2-Butylcyclohexanone
• carbanions
• α-cumylpotassium
• epoxides
• organometallic reagents
• semicarbazone

ACKNOWLEDGMENTS

We gratefully acknowledge the support of the Department of Chemistry and Graduate School of the University of Texas at El Paso and the funding provided by the Louis Stokes Alliance for Minority Participation Bridge to the Doctorate Fellowship (HRD-0832951). We also acknowledge the generous donation of potassium tert-amylate by BASF.