Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (16): 1657-1662. Previous Articles     Next Articles

Original Articles

α-单取代环十二酮肟及缩氨基硫脲的合成及晶体结构

王明安, 闫晓静, 刘建平, 金淑惠, 李太公, 杨旭, 王道全*   

  1. (中国农业大学应用化学系 北京 100094)
  • 投稿日期:2007-03-29 修回日期:2007-06-21 发布日期:2007-08-28
  • 通讯作者: 王道全

Synthesis and Crystal Structure of α-Monosubstituted Cyclododecanone Oxime and Thiosemicarbazone

WANG Ming-An; YAN Xiao-Jing; LIU Jian-Ping; JIN Shu-Hui; LI Tai-Gong; YANG Xu; WANG Dao-Quan*   

  1. (Department of Applied Chemistry, China Agricultural University, Beijing 100094)
  • Received:2007-03-29 Revised:2007-06-21 Published:2007-08-28
  • Contact: WANG Dao-Quan

Two kinds of α-monosubstituted cyclododecanone oximes and thiosemicarbazones were synthesized by the reaction of α-monosubstituted cyclododecanone with hydroxylamine and 4-p-tolylthiosemicarbazide. The X-ray diffraction analysis showed that they had different conformations, in which the parent ring takes still [3333] conformation and the substituting group is at α-side-exo or a-corner-anti position. These results were rationalized by “corner-position carbonyl participation” of raw materials, “memory effect” and H-bonding between hydroxylamine or 4-p-tolylthiosemicarbazide and α-monosubstituted cyclododecanone. In general, an amine molecule approaches cyclododecanone from the side with less hindrance, resulting in α-corner-anti monosubstituted cyclododecanone oximes or thiosemicarbazones, whereas an approach of an amine molecule from the other side where hydrogen bonding occurs gives rise to α-side-exo monosubstituted cyclododecanone oximes or thiosemicarbazones.

Key words: α-monosubstituted cyclododecanone oxime, α-monosubstituted cyclododecanone thiosemicarbazone, crystal structure, corner-position carbonyl participation, memory effect