New Synthesis of Organofluorine Compounds Using Solid-Liquid Interface

1993 Fiscal Year Final Research Report Summary

• Project/Area Number: 04640500
• Research Category: Grant-in-Aid for General Scientific Research (C)
• Allocation Type: Single-year Grants
• Research Field: 有機化学一般
• Research Institution: Osaka University
• Principal Investigator: ICHIHARA Junko Osaka University, ISIR-SANKEN Technical Staff, 産業科学研究所, 教務職員 (60110772)
• Co-Investigator(Kenkyū-buntansha): ITO Yoshiaki Kyoto University, Institute of Chemical Research Research Associate, 化学研究所, 助手 (40223200) ; YAMATAKA Hiroshi Osaka University, ISIR-SANKEN Associate Professor, 産業科学研究所, 助教授 (60029907)
• Project Period (FY): 1992 – 1993
• Keywords: Solid-liquid interfacial reaction / Composite solid reagent / Organic fluorination / Organofluorine compound / Lead(II)fluoride / Aklyl halide / Calcium fluoride

Research Abstract

We have studied novel solid-liquid interfacial fluorination methodology by means of composite inorganic solid materials. We have recently observed that the potassium fluoride-calcium fluoride combined reagent is much more efficient for the fluoride displacement of benzy halides than potassium fluoride alone. Various factors influencing on the reactivity has been investigated in order to ellucidate the acceleration mechanisn and the following results was obtained. i. Calcium fluoride, which is porous and has much greater specific surface area, was effctive. ii. Powder X-ray diffraction analysis of the KF-CaF_2 reagent showed no chemical interaction between the two fluorides. iii. Calcium fluoride also accelerated nucleophikic substitution reactions with other inrganic salts such as potassium cyanide, potassium acetate, or potassium thiocyande. Thus, calciuym fluoride may desperse intrganic mucleophiles on its wide surface to enhance the nucleophilicity, possibly by physical interaction.