A new method was developed for the synthesis of 6-substituted 1,5-diazabicyclo[3.1.0]hexanes and 7-substituted 1,6-diazabicyclo[4.1.0]heptanes by condensation of N -monohalotrimethylene- and N -monohalotetramethylenediamines with carbonyl compounds in the presence of bases. X-ray diffraction studies and quantum-chemical B3LYP/6-31G* calculations demonstrated that the conformations of the resulting bicyclic systems are stabilized by stereoelectronic interactions. As a result, a boat conformation prevails in 1,5-diazabicyclo[3.1.0]hexanes, whereas the energies of chair, half-chair, and boat conformations of 1,6-diazabicyclo[4.1.0]heptanes are equalized.

中文翻译：

---

1,5-二氮杂双环[3.1.0]己烷和1,6-二氮杂双环[4.1.0]庚烷：一种合成，量子化学计算和X射线衍射研究的新方法

通过 N-单 卤代三亚甲基和 N-单 卤代四亚甲基二胺的缩合反应，开发了一种新的合成6-取代的1,5-二氮杂双环[3.1.0]己烷和7-取代的1,6-二氮杂双环[4.1.0]庚烷的 方法。碱存在下的羰基化合物。X射线衍射研究和量子化学B3LYP / 6-31G *计算表明，所形成的双环系统的构象通过立体电子相互作用得以稳定。结果，在1，5-二氮杂双环[3.1.0]己烷中盛行船形，而在椅子，半椅子和船形的1，6-二氮杂双环[4.1.0]庚烷中的能量相等。