The Chemistry of Phosphinic and Phosphinous Acid Derivatives Containing t-Butyl Group as a Single Bulky Substituent: Synthetic, Mechanistic and Stereochemical Aspects

Abstract

Basic synthetic procedures commonly applied for the preparation of racemic and optically active phosphinic and phosphinous acid derivatives containing a t-butyl group as a single bulky substituent are presented. Mechanistic and stereochemical aspects of the presented protocols are discussed. Structural studies, which include the X-ray and vibrational circular dichroism-based determinations of the absolute configuration at the stereogenic phosphorus atom and calculations of conformational equilibria for a few model compounds are also mentioned. The use of the optically active tbutylphenylthiophosphinic acid as a chiral solvating agent is illustrated. Keywords: t-Butylphenylphosphine sulfide, halogenation reaction, iodine oxidation, stereoselectivity, secondary chlorophosphines