Li Liu, Long Stephen M, Dolinar Brian S, Popp Brian V, Wang Kung K
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, United States.
ACS Omega. 2025 Jan 16;10(3):3222-3227. doi: 10.1021/acsomega.4c11201. eCollection 2025 Jan 28.
The Diels-Alder reactions between (,)-1,4-bis(4-bromophenyl)-1,3-butadiene and dienophiles and the use of the resulting adducts for macrocyclization and aromatization were established. Several functionalized macrocyclic structures bearing a functionalized [9]cycloparaphenylene or a higher homological unit were isolated. The distribution of the macrocyclic structures was found to be governed by the structures of the starting Diels-Alder adducts. An empirical correlation between the angles of the two 4-bromophenyl groups of the X-ray structures of the Diels-Alder adducts and the macrocyclization steps was observed.
确立了（±）-1,4-双（4-溴苯基）-1,3-丁二烯与亲双烯体之间的狄尔斯-阿尔德反应，以及所得加烯加成产物用于大环化和芳构化的用途。分离得到了几种带有官能化[9]环对亚苯基或更高同系单元的官能化大环结构。发现大环结构的分布受起始狄尔斯-阿尔德加成产物的结构控制。观察到狄尔斯-阿尔德加成产物的X射线结构中两个4-溴苯基的角度与大环化步骤之间存在经验相关性。
