Chemical Communications

Highly efficient synthesis of [3]-and [5]-rotaxanes consisting of crown ether and a sec-ammonium salt

N Watanabe, T Yagi, N Kihara, T Takata

Index: Watanabe, Nobuhiro; Yagi, Takaya; Kihara, Nobuhiro; Takata, Toshikazu Chemical Communications, 2002 , # 22 p. 2720 - 2721

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Citation Number: 33

Abstract

The synthesis of [3]rotaxanes was achieved as shown in Scheme 1. Primary diamines were converted to bisammonium salt 1via condensation with methyl 4-formylbenzoate, followed by LiAlH 4 reduction and protonation. The synthesis of the rotaxanes was carried out in CH 2 Cl 2 –CH 3 CN mixed solvent since the pseudorotaxane derived from the bisammonium salts was insoluble in less polar solvents. Although the axles (1a–d) were insoluble in CH 2 Cl 2 –CH 3 CN (1∶1) at ...