Reactions of the Cyclopropanone Hemiketal Magnesium Salt with Some Nucleophilic Reagents

Article abstract of DOI:10.1021/jo01309a012

Cyclopropanol (5), 1-(arylethynyl)cyclopropanol (7), 1-(3-hydroxypropyl)cyclopropanol derivative 10, 1-(2-propynyl)cyclopropanol (14), cyclopropanone cyanohydrin (19), 1-(aminomethyl)cyclopropanol (21) derivatives, benzylidenecyclopropanes 32, and ethyl cyclopropylideneacetate (38) have been prepared from the magnesium salt of cyclopropanone hemiketal 3. 3-Cyclopropylidene-1-propanol (12) and 3-cyclopropylidene-1-propyne (16) have been obtained from the cyclopropanols 10 and 14, respectively. Some reactions of this new synthon were specific. On the other hand, 3 did not undergo the nucleophilic addition of sulfur and nitrogen ylides; it underwent oxidizing ring opening with BrZnCH2COOEt and induced the decomposition of diazomethane.