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Tripodands with Phenyl and Thiophenyl Rings and Nitrogen Bridgehead Atoms
Author(s) -
Baier Martin,
Gleiter Rolf,
Rominger Frank
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600512
Subject(s) - chemistry , phenylacetylene , iodide , sonogashira coupling , aryl , heteroatom , trifluoromethanesulfonate , crystallography , intermolecular force , amine gas treating , halide , hydrogen bond , polymer chemistry , synthon , hydrogen iodide , stacking , stereochemistry , palladium , organic chemistry , alkyl , molecule , iodine , catalysis
The flexible tripodands 7 – 9 and 15 with phenyl and thiophenyl rings as “legs” and nitrogen as bridgehead atoms have been synthesized by three‐component condensation reactions of the corresponding amine with the aryl halide. The more rigid species 10 – 14 and 17 were built up from the podands 7 – 9 as well as from their iodine substitution products 33 – 35 by a sequence of ethynylation and C–C coupling reactions. Podand 16 was prepared from tris‐iodide 36 by Sonogashira coupling with phenylacetylene. In the cases of 7 , 12 , 15 – 17 , 22 , 24 , 35 , 36 , and 41 the structural parameters were determined by X‐ray studies. With the exception of 7 , 12 , and 17 , all structures show either close intermolecular contacts between heteroatoms ( 15 , 22 , 24 , 35 , and 36 ), C–H ··· N hydrogen bonding ( 41 ), or are closely packed as a result of π ··· π stacking ( 16 ). We were able to isolate silver triflate complexes of 9 , 10 , and 16 , and in the case of 9 we obtained crystals suitable for X‐ray diffraction studies. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)