The chemistry of small ring compounds. Part 26. The chemistry of 1‐(dimethylamino)cyclopropanol

Abstract

Abstract The hydroxyl group of the title compound can easily be displaced by all common nucleophiles. The mechanism of such displacements is discussed in terms of an S N 1 type reaction involving the cyclopropaniminium ion as an intermediate. An explanation is given why weak acids are good catalysts for such displacements, while mineral acids are poor. The reaction of 1‐(dimethylamino)cyclopropanol with ketene and isocyanates leads to the formation of transient cyclopropanone. Ketene and isocyanates do not react simply with the hydroxyl group of 1‐(dimethylamino)cyclopropanol, but form derivatives of dimethylamine besides the liberated cyclopropanone.