The Chemistry of Small Ring Compounds. Part 231Improved Synthesis of Cyclopropanone and Some 1-Substituted Cyclopropanols
- 1 January 1973
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 3 (3) , 189-196
- https://doi.org/10.1080/00397917308062034
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 nucleophiles6,7, and many of the resulting 1-substitutedKeywords
This publication has 8 references indexed in Scilit:
- The chemistry of small ring compounds. Part 19 the N,N-dimethylcyclopropaniminium ionTetrahedron Letters, 1972
- Cyclopropanones. IV. 1-piperidinocyclopropanol and related systemsTetrahedron Letters, 1970
- CyclopropanonesAccounts of Chemical Research, 1969
- Cyclopropanones—VIIITetrahedron, 1968
- The chemistry of cyclopropanones. Part IV: Addition of mono‐ and di‐methylamineRecueil des Travaux Chimiques des Pays-Bas, 1967
- Cyclopropanone1Journal of the American Chemical Society, 1966
- The synthesis of cyclopropanone: Short communicationRecueil des Travaux Chimiques des Pays-Bas, 1966
- Oxidation of cyclopropanone hydrate and hemiacetal by metal ions: (Preliminary communication)Recueil des Travaux Chimiques des Pays-Bas, 1966