title: Acceleration of Acid-Catalyzed Hydrolysis in a Biphasic System by Sodium Tetracyanocyclopentadienides.
abstract: The hydrolysis of tert-butyldimethylsilyl L-menthyl ether (3) in a CH2Cl2-1 M HCl biphasic solvent system was accelerated by the addition of sodium tetracyanocyclopentadienides 1. Particularly, the reaction rate was enhanced using sodium salt 1a-c with a lipophilic substituent on the cyclopentadienide ring. From the results obtained by a triphasic experiment, hydrolysis proceeds via the formation of hydronium ion 2 in the aqueous phase by ion exchange, followed by the transfer of 2 to the CH2Cl2 phase.
authors.affiliation: Faculty of Pharmacy, Meijo University.
authors.forename: Takeo
authors.initials: T
authors.lastname: Sakai
authors.forename: Mariko
authors.initials: M
authors.lastname: Bito
authors.forename: Makoto
authors.initials: M
authors.lastname: Itakura
authors.forename: Honami
authors.initials: H
authors.lastname: Sato
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mori
mesh_terms: D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry*; D006851:Hydrochloric Acid / Q000737:chemistry*; D006868:Hydrolysis; D008752:Methylene Chloride / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D003517:Cyclopentanes; D017646:Organosilicon Compounds; D012997:Solvents; D008752:Methylene Chloride; D006851:Hydrochloric Acid