Bonifacio Margel C, Robertson Charles R, Jung Jun-Young, King Benjamin T
Department of Chemistry, University of Nevada, Reno, Nevada, 89557, USA.
J Org Chem. 2005 Oct 14;70(21):8522-6. doi: 10.1021/jo051418o.
A strategy for the synthesis of polycyclic aromatic hydrocarbons (PAHs) by the ring-closing olefin metathesis (RCM) of pendant olefins on a phenylene backbone has been developed. RCM of 2,4',6',2' '-tetravinyl-[1,1';3',1' ']terphenyl and 2,2',5',2' '-tetravinyl-[1,1';4',1']terphenyl affords in high yield the isomeric [a,j] and [a,h] dibenzanthracenes, respectively. In contrast with other intramolecular annulation methods, such as Friedel-Crafts acylations, this reaction is completely regioselective. Since RCM is reversible and PAHs are often thermodynamic sinks, this strategy is an effective and general method for the preparation of PAHs. Density functional theory calculations support these results. Carbon disulfide is a suitable solvent for these reactions.
一种通过亚苯基主链上侧链烯烃的闭环烯烃复分解反应（RCM）合成多环芳烃（PAHs）的策略已经开发出来。2,4',6',2''-四乙烯基-[1,1';3',1'']三联苯和2,2',5',2''-四乙烯基-[1,1';4',1']四联苯的RCM反应分别以高产率得到异构体[a,j]和[a,h]二苯并蒽。与其他分子内环化方法（如傅克酰基化反应）相比，该反应具有完全的区域选择性。由于RCM是可逆的，且多环芳烃通常是热力学阱，因此该策略是制备多环芳烃的一种有效且通用的方法。密度泛函理论计算支持了这些结果。二硫化碳是这些反应的合适溶剂。
