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SYNTHESIS, STRUCTURE, AND THEORETICAL CALCULATIONS OF 1H-3,7-DIFURYLCYCLOPENTA[3,4-d]PYRIDAZINE

  作者 SNYDER CHAD A; TICE NATHAN C; MADDOX JEREMY B; PARKIN SEAN; DANIEL AARON W; THOMAS JARON M  
  选自 期刊  Heterocycles;  卷期  2011年83-6;  页码  1275-1290  
  关联知识点  
 

[摘要]Treating [M{eta(5)-1,2-C(5)H(3)(COC(4)H(3)O)(2)}(CO)(3)] (3) (M = Mn, 3A, M = Re, 3B) with excess hydrazine hydrate in methanol afforded the desired 5,6-fused ring pyridazine complexes, [M(CO)(3){eta(5)-1,2-C(5)H(3)(CC(4)H(3)ON)(CC(4)H(3)ON)}] (4) (M = Mn, 4A, M = Re, 48), in high yield (76%). However, when X-ray crystallographic analysis of the pyridazyl complexes 4A and 4B was attempted, all recrystallization trials led to ligand loss to the 1,2-difurylpyridazine, 1,2-C(5)H(3)(CC(4)H(3)ONH)(CC(4)H(3)ON) (5). Compound 5 was observed to have a coplanar stacking arrangement in the solid state along the crystallographic b axis. Theoretical calculations performed on compound 5 indicate a high degree of intramolecular electronic delocalization as well intermolecular orbital interaction.

 
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