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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (11): 1448-1450. 上一篇    下一篇

研究简报

烯丙基溴化钐与α,β-不饱和醛酮反应合成高烯丙基醇

余明新*, 张永敏   

  1. 浙江大学化学系 杭州 310027
  • 收稿日期:2003-12-01 修回日期:2004-03-29 接受日期:2004-05-18 发布日期:2022-09-21
  • 通讯作者: * E-mail: mingxinyu@zju.edu.cn
  • 基金资助:
    国家自然科学基金(No. 29872010)资助项目.

Synthesis of Homoallyl Alcohol by the Reaction of Allylsamarium Bromide with α,β-Unsaturated Aldehydes and Ketones

YU Ming-Xin*, ZHANG Yong-Min   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310027
  • Received:2003-12-01 Revised:2004-03-29 Accepted:2004-05-18 Published:2022-09-21

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烯丙基溴与金属钐在室温条件下、THF溶剂中反应生成中间体烯丙基溴化钐,烯丙基溴化钐再与α,β-不饱和醛、酮反应生成高烯丙基醇.烯丙基溴化钐与α,β-不饱和醛、酮发生1,2-加成反应,其与α,β-不饱和酮的反应几乎定量进行,表明该反应具有很好的区域选择性.产物的结构通过IR, 1H NMR和MS光谱确证.

关键词: 烯丙基溴化钐, 高烯丙基醇, 加成反应, 区域选择性

Allylsamarium bromide, prepared by the reaction of allyl bromide with samarium in THF at room temperature, reacted via 1,2-additionwith α,β-unsaturated aldehydes or ketones to give homoallyl alcohol. Thequantitative addition of allylsamarium bromide to α,β-unsaturated ketonesis a satisfactory display of regioselectivity. The structures of products werecharacterized by IR, 1H NMR and MS spectra.

Key words: allylsamarium bromide, homoallyl alcohol, addition, regioselectivity