Nucleophilic displacement reactions in ionic liquids: substrate and solvent effect in the reaction of NaN3 and KCN with alkyl halides and tosylates

C Chiappe, D Pieraccini, P Saullo

Index: Chiappe, Cinzia; Pieraccini, Daniela; Saullo, Paola Journal of Organic Chemistry, 2003 , vol. 68, # 17 p. 6710 - 6715

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Citation Number: 127

Abstract

Room-temperature ionic liquids have been used as environmentally benign solvents for the preparation of primary and secondary alkyl azides and nitriles under solid-RTIL phase- transfer conditions. The reaction of primary, secondary, and tertiary halides or tosylates with KCN and NaN3 has been investigated in three ionic liquids ([bmim][PF6],[bmim][N (Tf) 2], and [hpyr][N (Tf) 2]). The observed nucleofugacity scales for the reaction of NaN3 are ...