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The stereochemistry of thionation reaction of 2 -substituted 4 -aryl- 5, 5 dimethyl - 1. 3. 2 -dioxaphosphorian-ones 1a-r with Lautssen’s reagent (LR ) was reported in this paPer. The results indicated that the thionation reaction of LR proceeded predominantly with retention of configuration.The mechanism leading to retention was proposed by assuming a cyclic pentacoordinated intermidiate.