化学学报 ›› 1988, Vol. 46 ›› Issue (2): 155-158. 上一篇    下一篇

研究论文

叔胺存在下的反常Reimer-Tiemann反应

丁新腾;张琳;葛羽   

  1. 复旦大学化学系
  • 发布日期:1988-02-15

The behavior of Reimer-Tiemann reaction under the influence of tertiary amines

DING XINTENG;ZHANG LIN;GE YU   

  • Published:1988-02-15

经典的Reimer-Tiemann反应的主要产物为邻位羟基取代苯甲醛类化合物,对位羟基取代苯甲醛类化合物为次要产物,其量甚少.在叔胺存在下,可使Reimer-Tiemann反应产物中对位羟基取代苯甲醛类化合物为主要产物,相应的邻位产物则成为次要产物,称这种反应为反常Reimer-Tiemann反应.本文对反常Reimer-Tiemann反应的反应条件进行探讨,并提出了反应机理.

关键词: 苯酚 P, 苯甲醛 P, 叔胺, 氯仿, 丁胺 P, 苯甲醇, REIMER-TIEMANN反应

In the presence of a tertiary amine, phenols underwent an abnormal Reimer-Tiemann reaction, i.e., the ratio of the para- and ortho-products was reversed. For example, phenol gave 60% yield of p-hydroxybenzaldehyde, 7% yield of o-hydroxybenzaldehyde and 1% of tarry materials. Whereas in the absence of the tertiary amines, the yield of para-, ortho-, and tarry materials under the optimum conditions were 8-11, 38-45 and 20% resp. The conditions of the abnormal Reimer-Tiemann reaction were studied in detail and a mechanism was proposed. o-Methylphenol, and o-methoxyphenol underwent the above abnormal Reimer-Tiemann reaction similarly.

Key words: PHENOL P, BENZALDEHYDE P, TERTIARY AMINE, CHLOROFORM, BUTANAMINE P, BENZALCOHOL, REIMER-TIEMANN

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