The Chemistry of Small Ring Compounds. Part 23¹ Improved Synthesis of Cyclopropanone and Some 1-Substituted Cyclopropanols

Abstract

Cyclopropanone, the simplest member of the cyclic ketones, has fascinated organic chemists for decades. Although its (attempted) synthesis was reported as early as 1890², its first preparation dates back to 1932, when Lipp³ et al. succeeded in isolating 1,1-dihydroxycyclopropane from the reaction of diazomethane with an excess of ketene. Much later, in 1966, Schaafsma¹ succeeded in isolating the free ketone prepared iron the same reagents by using liquid propane as the solvent. At about the same time, the (dissolved) ketone was also characterized by Turro and Hammond.⁵ Cyclopropanone undergoes a rapid reaction with all types of nucleophiles^6,7, and many of the resulting 1-substituted