Ying Weijiang, Zhang Lei, Wiget Paul A, Herndon James W
Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003 USA.
Tetrahedron Lett. 2016 Jul 6;57(27-28):2954-2956. doi: 10.1016/j.tetlet.2016.05.059. Epub 2016 May 17.
Substituted hydronaphthalenes where each of the ten carbons of the two-ring system contains functionality were obtained through a tandem [8+2] cycloaddition and base-catalyzed rearrangement process using dienylfurans and electron-deficient alkynes. If the [8+2] process is conducted under solvent-free conditions the process could be conducted in a single reaction flask without isolation of the chromatographically sensitive [8+2] cycloadducts. A mechanism involving base catalysed alkene positional isomerization followed by disrotatory electrocyclic ring closure was proposed for the key reaction step that converts [8+2] cycloadducts to hydronaphthalenes. The products undergo selective ring opening-isomerization processes upon treatment with Lewis acids.
通过使用二烯基呋喃和缺电子炔烃的串联[8+2]环加成和碱催化重排过程，获得了双环系统的十个碳原子中的每一个都含有官能团的取代氢化萘。如果[8+2]过程在无溶剂条件下进行，则该过程可以在单个反应烧瓶中进行，而无需分离对色谱敏感的[8+2]环加成物。对于将[8+2]环加成物转化为氢化萘的关键反应步骤，提出了一种涉及碱催化的烯烃位置异构化，随后进行顺旋电环化闭环的机理。在用路易斯酸处理时，产物会发生选择性的开环异构化过程。
