Factors in the formation of isomerically and optically pure alkyl halides. Part IX. Reactions of (1-substituted n-alkyl) diphenylphosphinites with hydrogen halides and with halogens

Abstract

1-Substituted n-alkyl chlorides and bromides are obtained in high yield, and with no detectable rearrangement, by the interaction of the corresponding alkyl diphenylphosphinites with hydrogen halides or with halogens at 0–20 °C. A slight tendency to the formation of rearrangement products is shown in the iodide systems, although products of at least 99.5% purity are obtainable if the reaction time is restricted. Optically active 2-chloro-octane is readily obtained with no loss in optical purity, although the bromide and iodide are liable to undergo some racemization after their initial formation.