scholarly journals Synthesis of Cyclic Guanidines Fused with Aromatic Ring through Metal Ion Promoted Cyclization

1983 ◽  
Vol 56 (10) ◽  
pp. 3189-3190 ◽  
Author(s):  
Hiroyuki Obase ◽  
Nobuhiro Nakamizo ◽  
Haruki Takai ◽  
Masayuki Teranishi
Keyword(s):  
2009 ◽  
Vol 62 (10) ◽  
pp. 1246 ◽  
Author(s):  
Ian J. Clark ◽  
Alessandra Crispini ◽  
Paul S. Donnelly ◽  
Lutz M. Engelhardt ◽  
Jack M. Harrowfield ◽  
...  

Dedication: One of Alan Sargeson’s great abilities was to seek out knowledge on topics of which he was not the master from those people with the expertise. This led occasionally to publications with a ‘cricket team’ of authors but with a rich brew of information, often international. Alan also insisted that all authors were equal since, without any one, the paper would not be what it was. Hence, he endeavoured to pursue the policy, difficult to maintain over a period where an obsession with absurdities such as the order of authors and point-scoring based on meaningless publication indices became so important in the maintenance of research, of listing authors simply in alphabetical order. In describing work begun while he was still with us, we have attempted to adhere to his principles. Analysis of a body of crystallographic information concerning metal(ii) and metal(iii) complexes of macrobicyclic hexamine ligands and some of their derivatives provides evidence for the action of a variety of intermolecular forces within the lattices. Hydrogen bonding is universal and its forms depend strongly upon the oxidation state and the particular nature of the metal ion bound to the macrobicycle. The introduction of both aliphatic and aromatic substituents leads to lattices in which these substituents associate, although, in the case of aromatic substituents, this is not necessarily a consequence of ‘π-stacking’, despite the fact that the aromatic ring planes form parallel arrays. At least in the case of CoIII, stable enantiomers of the complexes can be obtained, and in {Δ-(+)589-[Co{(NH3)(CH3)sar}]}2Cl2(C6(CO2)6)·26H2O (sar = 3,6,10,13,16,19-hexa-azabicyclo[6.6.6]icosane), the benzene hexacarboxylate anion adopts a chiral conformation in the presence of the optically active cation.


1979 ◽  
Vol 37 ◽  
pp. L511-L512 ◽  
Author(s):  
Michal Sabat ◽  
Malgorzata Jecżowska ◽  
Hnery Koz$z.xl;lowski

1993 ◽  
Vol 51 (1-2) ◽  
pp. 113
Author(s):  
Akira Odani ◽  
Tatsuo Yajima ◽  
Hideki Masuda ◽  
Osamu Yamauchi

2004 ◽  
Vol 59 (11-12) ◽  
pp. 1471-1479 ◽  
Author(s):  
Rixa von Bülow ◽  
Stephan Deuerlein ◽  
Thomas Stey ◽  
Regine Herbst-Irmer ◽  
Heinz Gornitzka ◽  
...  

A ‘carbanion’ can coordinate to a metal like an ‘amide’ if there is a nitrogen atom present to withdraw electron density from the formally negatively charged carbon center. On the other hand, shifting the negative charge from the amido nitrogen atom to the carbon substituent should convert an ‘amidic’ into a ‘carbanionic’ coordination behavior. This seems feasible with various substituents at the aromatic ring in a primary amide. This paper is concerned with the influence of aromatic substitution, as well as with the nature of the metal ion on the coordination mode of an amide ligand. Discussed are the parent lithium anilide [(thf)2LiNH(C6H5)]2 (1), the pentafluorinated lithium anilide [(thf)2LiNH(C6F5)]2 (2) and the lithium amino benzonitrile [(thf)2LiNH(C6H4pCN)]2 (3). All amide ligands coordinate the lithium cation exclusively with their amido nitrogen atom. In the dimeric structure of 1 the atom can be regarded to be sp2-hybridized. Fluorine substitution of the ring results in a slightly more pronounced coupling of the negative charge to the aromatic ring. A para-nitrile group further enhances quinoidal perturbation of the C6-perimeter from six-fold symmetry. Consequently, the ipso- and ortho-carbon atoms of the ring are partially negative charged. Those carbon atoms are only attractive for the soft rubidium cation in an aza allylic coordination in [(thf)2RbNH(C6H4pCN)]n (4) but not to the hard lithium cation.


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