For faster navigation, this Iframe is preloading the Wikiwand page for 亚砜.

亚砜

维基百科,自由的百科全书

亚硫酰基
亚硫酰基

亚砜是含有亚硫酰基(>S=O)官能团的一类有机化合物,可由硫醚氧化得到。常见的亚砜有氯化亚砜二甲基亚砜、二苯基亚砜等。

性质

亚砜的通式为R-S(=O)-R',其中R和R'是有机基团。亚砜中的成键与氧化叔膦(R3P=O)类似,由于电负性差异,S=O键中,硫显正价,氧显负价:

亚砜

硫原子为四面体结构,有一对孤对电子,类似于sp3杂化的碳原子。当硫所连接的两个基团不相同时,就会产生手性,比如甲基苯基亚砜

四面体结构

有时构型转换所需的能量相当高,室温下的外消旋速率很慢,以至于对映体相对稳定。有些手性的亚砜在医药中有应用,比如埃索美拉唑和阿莫达非。此外,亚砜也被用作手性辅助剂。[1]

反应

亚砜中硫的氧化态为0,处于硫醚(-2)和(+2)之间。因此氧化硫醚时,依次会得到亚砜、砜。例如氧化二甲基硫醚时可以得到二甲基亚砜二甲基砜。很多有手性的亚砜可从非手性的硫醚为原料,在过渡金属和手性配体的存在下以不对称催化氧化反应合成。

亚砜可由强碱如氢化钠去质子化[2],很多亚砜(如DMSO)都是很好的配体烷化剂

参考资料

  1. ^ Gama, Ángeles; Flores-López, Lucía Z.; Aguirre, Gerardo; Parra-Hake, Miguel; Hellberg, Lars H.; Somanathan, Ratnasamy. Ramsden, Christopher A. , 编. Oxidation of sulfides to chiral sulfoxides using Schiff base-vanadium (IV) complexes. Arkivoc. 2003-09-09, 2003 (11): 4–15 [2022-03-05]. ISSN 1551-7012. doi:10.3998/ark.5550190.0004.b02. (原始内容存档于2022-03-05) (英语). 
  2. ^ Iwai, I.; Ide, J. "2,3-Diphenyl-1,3-Butadiene" Organic Syntheses, Collected Volume 6, p.531 (1988). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV6P0531.pdf[永久失效链接].
{{bottomLinkPreText}} {{bottomLinkText}}
亚砜
Listen to this article

This browser is not supported by Wikiwand :(
Wikiwand requires a browser with modern capabilities in order to provide you with the best reading experience.
Please download and use one of the following browsers:

This article was just edited, click to reload
This article has been deleted on Wikipedia (Why?)

Back to homepage

Please click Add in the dialog above
Please click Allow in the top-left corner,
then click Install Now in the dialog
Please click Open in the download dialog,
then click Install
Please click the "Downloads" icon in the Safari toolbar, open the first download in the list,
then click Install
{{::$root.activation.text}}

Install Wikiwand

Install on Chrome Install on Firefox
Don't forget to rate us

Tell your friends about Wikiwand!

Gmail Facebook Twitter Link

Enjoying Wikiwand?

Tell your friends and spread the love:
Share on Gmail Share on Facebook Share on Twitter Share on Buffer

Our magic isn't perfect

You can help our automatic cover photo selection by reporting an unsuitable photo.

This photo is visually disturbing This photo is not a good choice

Thank you for helping!


Your input will affect cover photo selection, along with input from other users.