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Thiacrown Ethers with Oxygen and Sulfur for Coordination: Formation of the Pd and Pt Complexes and Pseudorotaxane with Dialkylammonium
Author(s) -
Nagai Hiroyuki,
Suzaki Yuji,
Osakada Kohtaro
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201402465
Subject(s) - chemistry , rotaxane , sulfur , polymer chemistry , crown ether , ether , metathesis , oxygen , medicinal chemistry , oxygen atom , ring (chemistry) , supramolecular chemistry , organic chemistry , molecule , polymerization , ion , polymer
Mono‐, di‐ tri‐, and tetrathiadibenzo[24]crown‐8‐ethers with eight oxygen or sulfur atoms within the 24‐menbered ring have been synthesized by using 1,2‐benzenedithiol and 2‐hydroxythiophenol as the starting materials. The thia[24]crown ethers form [2]pseudorotaxanes with dibenzylammonium salts, the association constants of which vary depending on the numbers and positions of the sulfur and oxygen atoms. The [2]pseudorotaxane of 1,4‐dithiadibenzo[24]crown‐8‐ether (1,4‐DTC) was converted into its Pd complex [PdCl 2 (1,4‐DTC)] by the addition of [PdCl 2 (cod)] (cod = 1,5‐cyclooctadiene), accompanied by the liberation of dibenzylammonium. Subsequent addition of PPh 3 to the mixture led to regeneration of the [2]pseudorotaxane. A [2]pseudorotaxane composed of 1,4‐DTC and dialkylammonium with two vinyl groups at both ends of the axis component underwent a cross‐metathesis reaction with an acrylate ester to form the corresponding [2]rotaxane with an interlocked structure.