Efficient synthesis of calix [6] tmpa: a new calix [6] azacryptand with unique conformational and host–guest properties

X Zeng, D Coquière, A Alenda, E Garrier…

Index: Zeng, Xianshun; Coquiere, David; Alenda, Aurelie; Garrier, Eva; Prange, Thierry; Li, Yun; Reinaud, Olivia; Jabin, Ivan Chemistry - A European Journal, 2006 , vol. 12, # 24 p. 6393 - 6402

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Citation Number: 69

Abstract

Abstract A new C 3v-symmetrical calix [6] azacryptand, that is, calix [6] tmpa (11), was synthesized by efficient [1+ 1] macrocyclization reactions. Remarkably, both linear and convergent synthetic strategies that were applied lead to equally good overall yields. Calix [6] tmpa behaves as a single proton sponge and appeared reluctant to undergo polyprotonation, unlike classical tris (2-pyridylmethyl) amine (tmpa) derivatives. It also acts ...