| STUDIES ON CHIRAL THIOPHOSPHORIC ACIDS AND THEIR DERIVATIVES [ⅤⅢ]——THE STEREOCHEMISTRY OF SOME REACTIONS OF THE MIXED ANHYDRIDE OF O-ETHYL PHENYLPHOSPHONOTHIOIC AND O-ETHYL O-PHENYL PHOSPHOROTHIOIC ACIDS |
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| 引用本文： | 唐除痴,唐永军,陈茹玉.STUDIES ON CHIRAL THIOPHOSPHORIC ACIDS AND THEIR DERIVATIVES [ⅤⅢ]——THE STEREOCHEMISTRY OF SOME REACTIONS OF THE MIXED ANHYDRIDE OF O-ETHYL PHENYLPHOSPHONOTHIOIC AND O-ETHYL O-PHENYL PHOSPHOROTHIOIC ACIDS[J].中国科学B辑(英文版),1988(6). |
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| 作者姓名： | 唐除痴 唐永军 陈茹玉 |
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| 作者单位： | Institute of Elemento-Organic Chemistry，Nankai University，Tianjin，Institute of Elemento-Organic Chemistry，Nankai University，Tianjin，Institute of Elemento-Organic Chemistry，Nankai University，Tianjin |
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| 摘 要： | In this paper, (1) alkaline methanolysis, (2) acid methanolysis, (3) alkaline hydro-lysis, (4) aminolysis of (+)-(R)-(R)-mixed anhydride 1 of O-ethyl phenylphosphonothioic:and O-ethyl O-phenylphosphorothioic acid, (5) its reactions with KSH and (6) with PCl_5have been studied. The cleavage of P-O-P bonds in all the reactions studied has beenfound. In reactions (1)-(4), attacks of nucleophiles occur to the phosphorus atoms of phos-phonyl groups forming the products with inversion of configuration, while the configurationof the phosphorus atoms of phosphoryl groups which are not attacked is retained. Inreaction (5), the uncleophile -SH attacks the phosphorus atom of the phosphonyl group,but a racemic product results because of the formation of ph(EtO)P(S)~- which loseschirality; the configuration of the phosphorus atom of the phosphoryl group which is notattacked is still retained. In reaction (6), both the phosphonyl and phosphoryl groups arechlorinated giving as products (-)-(R)-thiophophonyl chloride 1
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