The Chemistry of 1,3-Glycol Derivatives. III. The Preparation of 1,1-Bis(1-hydroxyalkyl)cyclopropanes and Their Halogenation

Article abstract of DOI:10.1246/bcsj.53.146

By the reduction of 1,1-diacylcyclopropanes and their related compounds, several kinds of 1,1-bis(1-hydroxyalkyl)cyclopropanes have been prepared.Some of the stereoisomers were separated, and their configurations were determined by the NMR study of the 1,3-dioxanes prepared by the acetallization of the diols.The diols were subjected to halogenation.Although the reactions of meso- and dl-bis(1-hydroxyethyl)cyclopropanes with thionyl chloride and phosphorus pentachloride gave normal dichlorides, accompanied by slight skeletal rearrangements, the stereospecificities were rather low.With ZnCl2-HCl, the specificities were lost completely and large amounts of the homoallyl derivative were formed.The reaction mechanism is discussed.