Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA.
J Am Chem Soc. 2010 Aug 18;132(32):11004-5. doi: 10.1021/ja1056888.
Cyclobutenone was employed as a dienophile in Diels-Alder cycloadditions, provide diverse and complex cycloadducts in good yields. Experimental outcomes indicated cyclobutenone to be more reactive than either cyclopentenone or cyclohexenone. In addition, cycloadducts bearing a strained cyclobutanone moiety were able to undergo regioselective ring expansions to produce corresponding cyclopentanones, lactones, and lactams, which are otherwise difficultly obtained by direct Diels-Alder reactions.
环丁烯酮被用作 Diels-Alder 环加成中的亲二烯体，以高产率提供了多样且复杂的环加成产物。实验结果表明，环丁烯酮比环戊烯酮或环己烯酮更具反应性。此外，带有张力环丁酮部分的环加成产物能够进行区域选择性的环扩张，生成相应的环戊酮、内酯和内酰胺，这些产物通过直接 Diels-Alder 反应很难获得。
