Studies on Chiral Thiophosphoric Acids and Their Derivatives(Ⅻ)─Synthesis of the Optical Isomers of Insecticidal O-Methyl O-Phenyl S-Propyl Phosphorothiolate and Their Absolute Configuration

Chem. J. Chinese Universities ›› 1994, Vol. 15 ›› Issue (9): 1327.

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Studies on Chiral Thiophosphoric Acids and Their Derivatives(Ⅻ)─Synthesis of the Optical Isomers of Insecticidal O-Methyl O-Phenyl S-Propyl Phosphorothiolate and Their Absolute Configuration

TANG Chu-Chi, MA Fu-Peng, ZHANG Mian-Ji, LI Zhen

Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071

Received:1993-09-18 Revised:1994-01-29 Online:1994-09-24 Published:1994-09-24

Abstract

Abstract: acemic O-methyl O-phenyl thiophosphoric acid 2 has been successfully resolved through its quinine and brucine salts in methanol solution by the fractional crystallization method. The optically active acids, ( +)-2 and(-)-2, react with propyl bromide in the presence of EtONa/EtOHto give(-)-O-methyl S-propyl O-phenyl phosphorothiolate 1 and(+)-1, respectively.The absolute configuration of the optically active 1 has been established as(-)-(S)and(+)-( R) by the chemical correlation method.

Key words: Phosphorothioate, Insecticide, Stereochemistry, Resolution, Absolute configuration

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TANG Chu-Chi, MA Fu-Peng, ZHANG Mian-Ji, LI Zhen. Studies on Chiral Thiophosphoric Acids and Their Derivatives(Ⅻ)─Synthesis of the Optical Isomers of Insecticidal O-Methyl O-Phenyl S-Propyl Phosphorothiolate and Their Absolute Configuration[J]. Chem. J. Chinese Universities, 1994, 15(9): 1327.

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Studies on Chiral Thiophosphoric Acids and Their Derivatives(Ⅻ)─Synthesis of the Optical Isomers of Insecticidal O-Methyl O-Phenyl S-Propyl Phosphorothiolate and Their Absolute Configuration

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