Han Xiaoqing, Zhang Yanzhong, Wang Kung K
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, USA.
J Org Chem. 2005 Mar 18;70(6):2406-8. doi: 10.1021/jo047745y.
[reaction: see text] Treatment of propargylic diols 5-7 with thionyl chloride promoted a cascade sequence of reactions leading to dichlorides 10-12 and, after reduction with tributyltin hydride, the diindeno-fused 4H-cyclopenta[def]phenanthrenes 13-15 in a single operation. Hydrolysis of 13 and 14 furnished 4H-cyclopenta[def]phenanthren-4-ones 16 and 17, respectively. Air oxidation of an alkaline solution of dichloride 11 produced diketone 18.
[反应：见正文] 用亚硫酰氯处理炔丙基二醇5 - 7引发了一系列串联反应，一步生成二氯化物10 - 12，并用三丁基氢化锡还原后得到二茚并稠合的4H - 环戊二烯并[def]菲13 - 15。13和14水解分别得到4H - 环戊二烯并[def]菲 - 4 - 酮16和17。二氯化物11的碱性溶液经空气氧化生成二酮18。
