Synthesis of Dibarrelane, a Dibicyclo[2.2.2]octane Hydrocarbon

The synthesis of a novel hydrocarbon, dibarrelane, has been accomplished in 11 steps via an intramolecular REDDA reaction of a masked o-benzoquinone, followed by Clemmensen reduction and Barton decarboxylation. The twisted structure of the tetracyclic dibarrelane skeleton was also clarified via X-ray crystallography. Finally, it was proposed that dibarrelane has C2 symmetry rather than C2v symmetry.本研究通过11步反应成功合成了新型烃类化合物二巴兰烷（dibarrelane）：以掩蔽邻苯醌（masked o-benzoquinone）为底物，先发生分子内REDDA反应，随后依次经克莱门森还原（Clemmensen reduction）与巴顿脱羧反应（Barton decarboxylation）完成合成。通过X射线晶体学（X-ray crystallography）明确了该四环二巴兰烷骨架的扭曲结构。最终研究提出，二巴兰烷的对称类型为C2对称，而非C2v对称。