1980•Bulletin of the Chemical Society of JapanRequires access
The Chemistry of 1,3-Glycol Derivatives. III. The Preparation of 1,1-Bis(1-hydroxyalkyl)cyclopropanes and Their Halogenation
Osamu Ito, Yoshiro Kohmura, Yasunori Ichikawa, M. Umezu, Tsutomu Okita, Katsuhiko Ichikawa
Open publisher page 7 citations
Abstract
Abstract 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.