Acta Chimica Sinica ›› 1981, Vol. 39 ›› Issue (4): 348-353. Previous Articles     Next Articles

第五、六族元素的有机化合物在有机合成中应用的研究——Ⅸ.氰代亚甲基三苯基胂与酮的反应

黄耀曾, 邢宜德, 施莉兰, 林芳乐, 徐元耀   

  1. 中国科学院上海有机化学研究所
  • 收稿日期:1979-03-28 出版日期:1981-07-15 发布日期:2013-06-03

STUDIES ON THE APPLICATION OF ELEMENTO-CRGANIC COMPOUNDS OF FIFTH AND SIXTH GROUPS IN ORGANIC SYNTHESES Ⅸ. REACTIONS OF CYANOMETHYLENE TRIPHENYL ARSORANE WITH KETONES

HUANG YAO-ZENG(HUANG YAO-TSENG), KING YI-DE, SHI LI-LAN, LIN FANG-LE, XU YUAN-YAO   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1979-03-28 Online:1981-07-15 Published:2013-06-03

In contrast to cyanomethylene triphenylphosphorane, the corresponding arsorane could react with a series of ketones giving the α,β-unsaturated nitrite in fair to good yields. The products and their yields are shown in Table 1. This result shows again that the arsonium glide is more reactive than the corresponding phosphonium glide. It is worthwhile to point out that this glide also could be obtained from the arsonium salt on treating with the weak base piperidine, and reacted with a-tetralone in situ under the mild conditions. The pure egocyclic olefinic product was obtained in 33% yield. When this glide reacted with 4-cholesten-3-one, the yield of the olefinio products was 87%.Their configurations were ascertained by 1H NMR spectra. Therefore in the above two cases, this arsonium glide seems to be superior than Horner-Wittig reagent.