化学学报 ›› 2001, Vol. 59 ›› Issue (10): 1697-1701. 上一篇    下一篇

研究论文

对羟基苯乙酮及其类似物的烷羰C----C键的断裂

高鹏;利群;王世玉;唐恢同;张滂   

  1. 北京大学化学与分子工程院
  • 发布日期:2001-10-15

A novel scission of alkyl-carbonyl C---C bond by alkyl p- hydroxyphenyl ketones

Gao Peng;Li Qun;Wang Shiyu;Tang Huitong;Zhang Pang   

  • Published:2001-10-15

甲基、乙基、正丙基和苄基对羟苯基酮和6-羟基甲氢萘-1-酮经证实在合成乙二醇缩酮的条件下发生烷羰C-C键的断裂,而对羟基二苯酮、对羟基苯异丁酮和5-羟基二氢茚-1-酮却不发生这一断键反应。经推论这一断键反应首先是发生羟醛缩合,继以在酚羟基参与下引发烷羰C-C键断裂的;还应指出,也是由于对位羟基的参与,这些烷基对羟苯基酮不形成它们的乙醇缩酮。

关键词: 苯乙酮P, 羟基化合物, 缩合反应, 茚酮, 碳-碳键, 断裂

Methyl, ethyl, n-propyl, and benzyl p-hydroxyphenyl ketones and 6- hydroxy-1-tetralone are shown under the condition of ethylene ketal formation to undergo alkyl-carbonyl C----C bond scission, but not with p-hydroxy-benzophenone, p-hydroxyisobutyrophenone, and 5-hydroxy- 1-indanone. It is suggested that the scission is preceded by an aldol condensation, followed by a phenolic hydroxyl participation with scission of the C---C in the β-hydroxy-ketone formed. It should be noted that the participation by phenolic hydroxyl is also the cause of nonformation ethylene ketals by those ketones mentioned.

Key words: ACETOPHENONE P, HYDROXYL COMPOUNDS, CONDENSATION REACTION, CARBON-CARBON BOND, FRACTURE

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