Synthesis of 4, 4′-bipentacyclo[5.4.0.02, 6.03, 10.05, 9]undecane. Issue 14 (5th April 2017)

• Record Type: Journal Article
• Authors: Shi, Yijun; Jiang, Jingyang; Ma, Li; Wang, Jianzhi; Li, Wei
• Is Part Of: Tetrahedron letters. Volume 58:Issue 14(2017)
• Page Start: 1376
• Page End: 1378
• Publication Date: 2017-04-05
• Subjects: Bi-cage hydrocarbon -- High-energy-density hydrocarbon -- 4, 4′-Bipentacyclo[5.4.0.02, 6.03, 10.05, 9]undecane -- 5, 5′-Bi(cyclopentadiene); Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.02.045
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new synthetic strategy to construct two cages simultaneously was designed. A new bi-cage hydrocarbon was synthesized through a three steps synthetic route. The bi-cage hydrocarbon has high density and high volumetric heat of combustion. The intramolecular [2+2] photocyclization can be carried out in sunlight. Abstract: A new bi-cage hydrocarbon, 4, 4′-bipentacyclo[5.4.0.0 2, 6 .0 3, 10 .0 5, 9 ]undecane (12 ) was designed based on a strategy to construct two cages simultaneously from one key molecule scaffold. Thus12 was conveniently synthesized from 5, 5′-bi(cyclopentadiene) (9 ) through a three steps synthetic route in 23% overall yield. The new bi-cage hydrocarbon has high density (1.2322 g/cm 3 ) and high volumetric heat of combustion (51.670 MJ/L).