By Gould R.F. (ed.)
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Oxidation of 218 with iodine in the presence of water occurred with inversion of configuration, again with high stereospecificity. With sulfur in the presence of N-methylmorpholine, the related phosphine sulfide 219 (X= S) is formed, again with the retention of c~nfiguration~~'. The course of the reaction of diphenylphosphine sulfide with dihaloalkanes depends on the length of the alkane chain, the nature of the halogen, and the conditions. With dihalomethanes, products are either the halomethylphosphine sulfide, or the reduction product diphenyl(methy1) phosphine sulfide.
Approach is the surface functionalisation of dendrimers bearing secondary amino groups, using hydroxymethyldiphenylphosphine, to form aminomethylphosphine ~ n i t s ' ~ ~ ~ ~ . approach A "similar has been used in the phosphino-functionalisation of aminoalkyl-P-cyclodextrin systems'88. , 139189. On treatment with aqueous sodium metabisulfite, 138 is converted into the primary phosphine 140, an air-stable orange solid"*. Formylation of the triphosphine 141 has given the new, water-soluble triphosphine 142'".
G. (S)-bornyl or (1 R)-isopinocamphenyl 212 213 K, 0 214 215 216 Chiral phosphine oxides 217 have been obtained in high enantiomeric purity by treatment of diastereoisomeric carbohydrate esters of methyl(pheny1)phosphinic acid with a Grignard reagent319. The optically-active phosphineborane 218 is oxidised to the phosphine oxide 219 ( X = O ) by m-chloroperbenzoic acid with almost complete retention of configuration at phosphorus. Oxidation of 218 with iodine in the presence of water occurred with inversion of configuration, again with high stereospecificity.