Ultrasonic acceleration of soild-liquid two-phase reaction. Facile aliphatic nucleophilic substitution with solid inorganic salts.

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  • 超音波による固‐液二相有機反応の促進　　無機塩固体試剤を用いる求核置換反応
  • チョウオンパ ニ ヨル コ エキ 2ソウ ユウキ ハンノウ ノ ソクシン ムキ

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Ultrasonic irradiation was found to accelerate a solid-liquid two-phase aliphatic nucleophilic substitution by cyanide, acetate, and thiocyanate ions in nonpolar organic solvents. This ac- celeration was prominent when an adequate inorganic solid support, namely alumina for cya- nide and silica gel for acetate and thiocyanate, was present in a heterogeneous reaction mix- ture. An interesting phenomenon of sonochemical switching of reaction pathways from aro- matic electrophilic to aliphatic nucleophilic substitution was reported for the reactions of benzyl bromides, potassium cyanide, and alumina in aromatic solvents. The effects of organic and inorganic additives and ultrasonic pretreatment on this switching were studied. From these observations as well as the X-ray and SEM study of sonicated potassium permanganate crystals, the possible factors of ultrasonic acceleration of a solid-liquid two-phase reaction with solid inorganic salts were estimated as follows: (1) increase in surface area and active sites on inorganic salt crystals, (2) promotion of the interaction between inorganic salts and solid supports, and (3) acceleration of the reaction itself with and without intervening water molecules.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1984 (11), 1731-1738, 1984

    The Chemical Society of Japan

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