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Synthesis 2001; 2001(4): 0647-0653
DOI: 10.1055/s-2001-12363
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Synthesis of Taddol-Derived Crown Ethers

José Irurre* , Marta Riera, M. Àngel Cintora
  • *Department of Organic Chemistry, Institut Químic de Sarrià (Universitat Ramon Llull), Via Augusta 390, 08017-Barcelona, Spain; Fax + 34-9 32 05 62 66; E-mail: jirur@iqs.es
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Publication Date:
31 December 2001 (online)

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Four cyclic polyethers incorporating one (4R,5R)-2,2-dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanol (2,2-dimethyl-TADDOL) unit and with ring sizes of 14-crown-4, 17-crown-5 and 20-crown-6 were synthesized. The synthesis of the corresponding bis(TADDOLo)-22-crown-6 ether was attempted, but the 11-crown-3 ether was obtained instead. The structures of the side-products were elucidated and their formation is rationalized on the basis of template and steric effects. The ability of the crown ethers synthesized, distorted by the presence of the TADDOL unit in the ring, to form host-guest complexes with alkali metal cations is briefly discussed.

TADDOLs - TADDOL-crown-ethers - synthesis of macrocycles - polyether rings - template effects - host-guest complexes

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