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烯酮

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烯酮通式
烯酮通式

烯酮是含有R2C=C=O结构的有机化合物的统称。赫尔曼·施陶丁格在烯酮研究方面作了很大贡献。[1]最简单的烯酮是乙烯酮,分子中两个R都是氢原子。

性质

由于积聚双键的存在,性质很活泼,易加成及聚合。

乙烯酮是无色有强烈气味的气体,刺激性和毒性很大,熔点-150.5°C(-239°F),沸点-56.1°C(-69°F)。

制备

由酰氯制备烯酮
三乙胺之类的碱可以脱去羰基alpha位的酸性氢,生成碳碳双键,氯离子离去。
  • alpha-重氮Wolff重排反应中转化为烯酮。
  • 苯乙酸alpha质子酸性较强,在碱存在下失水生成苯基烯酮。
  • 实验室中可由丙酮蒸汽热裂制取乙烯酮(CH2=C=O):[2]
CH3−CO−CH3 + Δ → CH2=C=O + CH4
乙烯酮的制备

反应

烯酮含有两个正交的π键,化学性质很活泼,是很好的酰基化试剂。

乙烯酮反应

它可以二聚生成二乙烯酮的衍生物,也可与富电子的炔烃发生[2+2]环加成反应生成环丁烯酮衍生物。

二乙烯酮反应

二醇(HO-R-OH)与二烯酮(O=C=CH-R'-CH=C=O)反应,生成聚酯含有(-O-R-O-CO-R'-CO-)重复单元。

乙烯酮与乙酸反应生成乙酸酐,工业上合成乙酸酐即是利用此法。

参见

参考资料

  1. ^ Staudinger, Hermann. Ketene, eine neue Körperklasse. Berichte der deutschen chemischen Gesellschaft. 1905-03, 38 (2): 1735–1739. ISSN 0365-9496. doi:10.1002/cber.19050380283 (英语). 
  2. ^ C. D. Hurd (1941). "Ketene页面存档备份,存于互联网档案馆)". Org. Synth.; Coll. Vol. 1: 330.
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烯酮
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