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化学学报
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化学学报 ›› 1965, Vol. 31 ›› Issue (5): 370-376,383. 上一篇    下一篇

论文

含官能团的取代烯烃的硼氢化反应——Ⅰ.巴豆醛的硼氢化反应

戴立信, 錢長濤   

  1. 中国科学院有机化学研究所
  • 投稿日期:1964-08-26 发布日期:2013-06-03

HYDROBORATION OF FUNCTIONALLY SUBSTITUTED OLEFINS Ⅰ. HYDROBORATION OF CROTONALDEHYDE

TAI LI-HSIN, CHIEN CHANG-TAO   

  1. Institute of Organic Chemistry, Academia Sinica
  • Received:1964-08-26 Published:2013-06-03

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巴豆醛在过量乙硼氢的硼氢化反应中得到的主要产物是正丁醇。本文论证这一反应的历程,其中包括有“二硼酸”型的β-消除反应。还讨论有电负性元素取代的烯烃的硼氢化反应。巴豆醛在低温(-25°)硼氢化,可使这类消除反应大为减少,主要得到硼氢化的正常产物——丁二醇。

The hydroboration of crotonaldehyde with excess of diborane (in ether, 0°)afforded n-butanol as the principal product. A reaction mechanism involving a diborate type β-elimination was proposed and verified. The hydroboration of olefins with electro-negative substituents is also discussed. The elimination during hydroboration was greatly suppressed at lower temperatures, and the normal hydroboration product (butandiol) was obtained predominantly.