12.4.5.4乌尔夫(Wolff)－凯惜纳(Kishner)－黄鸣龙反应
![](https://wkrtcs.bdimg.com/rtcs/image?w=20&md5sum=d435e5fbc66194d37ad8ce92f705c885&sign=d1106b866f&rtcs_flag=1&rtcs_ver=3.1&l=webapp&bucketNum=36&ipr={"t":"img","w":"20","h":"21","dataType":"png","c":"word/media/image1.png","imgOriW":20,"imgOriH":21})
常用于合成。
![](https://wkrtcs.bdimg.com/rtcs/image?w=467&md5sum=d435e5fbc66194d37ad8ce92f705c885&sign=d1106b866f&rtcs_flag=1&rtcs_ver=3.1&l=webapp&bucketNum=36&ipr={"t":"img","w":"467","h":"77","dataType":"png","c":"word/media/image2.png","imgOriW":467,"imgOriH":77})
醛或酮＋肼＋Na(或K)，高温(200℃)，高压式封管中进行
－Wolff-Kishner(反应) 还原法
黄鸣龙改进法：<请点击>
在肼、高b.p.水溶性 溶剂：
一缩二乙二醇 HOCH2CH2OCH2CH2OH（二甘醇） b.p. 245.5℃
三缩乙二醇 HO(CH2)2O·(CH2)2O(CH2)2OH（三甘醇） b.p. 287℃
用NaOH，KOH代替Na、K，加热
![](https://wkrtcs.bdimg.com/rtcs/image?w=380&md5sum=d435e5fbc66194d37ad8ce92f705c885&sign=d1106b866f&rtcs_flag=1&rtcs_ver=3.1&l=webapp&bucketNum=36&ipr={"t":"img","w":"380","h":"53","dataType":"png","c":"word/media/image3.png","imgOriW":380,"imgOriH":53})
先形成腙，在蒸发过量水及未反应肼，待反应升至腙，分解温度（200℃）继续回流至反应完成，可不使用纯肼，在常压下进行。
![](https://wkrtcs.bdimg.com/rtcs/image?w=17&md5sum=d435e5fbc66194d37ad8ce92f705c885&sign=d1106b866f&rtcs_flag=1&rtcs_ver=3.1&l=webapp&bucketNum=36&ipr={"t":"img","w":"17","h":"20","dataType":"png","c":"word/media/image1.png","imgOriW":20,"imgOriH":21})
较新改进：用二甲亚砜为溶剂，反应可在较低温下进行Clemmensen与Wolff－Kishner－黄鸣龙法互补。前者在H+下，适用于对碱敏感的醛酮后者在OH－下，适用于对酸敏感物。
