Synthesis and X-ray structural determination of new aniline derivatives of 2,4,6,8-tetraazabicyclo[3.3.0]octanes; anomeric effect in N-C-N moiety and implications of solvent polarity on 1H-NMR patterns
作者:Ali Kakanejadifard、S.Morteza F. Farnia
DOI:10.1016/s0040-4020(96)01143-x
日期:1997.2
8-tetraphenyl-2,4,6,8-tetraazabicyclo[3.3.0]octane (1f) with formic acid as catalyst. Nine substituted derivatives of 1f have been prepared in high yield by this synthetic method. X-ray analysis revealed the existence of an anomeric effect, in N-C-N moieties manifested by reduction in N-pyramidality and short CN bond lengths. Moreover, 1H-NMR studies showed the dependency of methylenic protons splitting pattern
以化学计量比将苯胺与乙二醛和甲醛缩合,生成2,4,6,8-四苯基-2,4,6,8-四氮杂双环[3.3.0]辛烷(1f),甲酸为催化剂。通过该合成方法已经高产率地制备了9个1f的取代衍生物。X射线分析揭示了NCN部分中存在异头作用,表现为N-金字塔性降低和CN键长度短。此外,1 H-NMR研究表明亚甲基质子分裂模式对溶剂极性的依赖性。