trans-Di-tert-butylcyclopropanone. Preparation, properties, resolution, and reaction with nucleophiles

JF Pazos, JG Pacifici, GO Pierson…

Index: Pazos,J.F. et al. Journal of Organic Chemistry, 1974 , vol. 39, p. 1990 - 1995

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Citation Number: 16

Abstract

The results are summarized in Chart 11. Conversion of hemiketal under basic conditions (ie, via the alkoxide species) to ester is rapid, and is easily understood. 15J6 Conversion of hemiketal to alkoxy ketone is slow, and the mechanism is less apparent. It probably involves reversion to the cyclopropanone, ring opening to oxyallyl species or the corresponding protonated form, and capture by solvent (eq 5). 17, 18