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Additional resources for Topics in Stereochemistry, Volume 3
P \ MeN”‘NMe -I-------- . / ~ an acid catalyst. Adamantane-type structures are formed from pentane2,4-dione and phosphine which, though more reactive than 40 are less so than acyclic phosphines. V. P(1V) COMPOUNDS A. Introduction Four-coordinated compounds form by far the largest group in phosphorus chemistry and only a limited treatment will be attempted here. The chemistry of condensed phosphates will be omitted and phosphonitrilic compounds will not be discussed as they have been reviewed elsewhere (7,119).
Raman and IR spectra of chloromethyl phosphonic dichloride (liquid) confirm the presence of two isomers; I R ofthe crystal showed only one form. Experiments with solvents of different polarity showed that the symmetrical form was present in the crystal, but the unsymmetrical form prevailed in the liquid state. Dialkylphosphinic chlorides (except the dimethyl compound) have been shown (230) to exhibit two P-C1 absorption bands as a result of P-C rotational isomerism. Rotational isomerism has been given some theoretical treatment (231-233).
Optically active thiophosphoryl halides are easily prepared from the corresponding acid by treatment with a P(V) halide. This reaction has been shown (126,128) to be at least 98% stereospecific by the sequence outlined in Figure 4. The reaction is proposed as occurring with inversion of configuration at phosphorus, perhaps via an intermediate such as 48 formed by initial attack of PCls on oxygen. Inversion in the formation of the acid chloride would require a further inversion in the formation of the P-0-P linkage as the product must have the same configuration as the original thio-acid.