Acta Chimica Sinica ›› 1983, Vol. 41 ›› Issue (10): 934-938. Previous Articles     Next Articles

Original Articles

应用锌-铜试剂进行7-氧杂双环[2,2,1]-庚-2,5-双烯化合物的去氧原子反应

邢宜德;龚菁菁;黄乃正   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1983-10-15

Extrusion of oxygen atom from the substituted 7-oxabicyclo (2,2,1)-hepta-2, 5-diene system by zinc-copper reagent

XING YIDE;GONG JINGJING;HUANG NAIZHENG   

  • Published:1983-10-15

The extrusion of oxygen atom from the 7-oxabicyclo (2, 2, 1)- hepta-2, 5-diene 1 to the substituted benzenes 2 is an interesting and important reaction. In the course of our continuing studies on the preparation of the substituted benzenoid compounds employing the deoxygenation reaction as the key step, we found that the zinc-copper reagent prepared according to the LeGoff procedure (increasing the amount of copper acetate to 3-4 fold) was also effective for such purpose. Thus, the reaction between zinc-copper reagent and the oxygen-bridged compounds 3a-c, 4 and 5 in refluxing THF furnished the compounds 6a-c, 7 and 8, respectively, the reaction conditions are shown in Table 1 in the Chinese Text. Their yields and physical constants are shown in Table 2.

Key words: REACTION MECHANISM, OXEPANE P, DIENE P, DEOXIDIZATION, ZINC-COPPER REAGENT

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