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硫醚

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FunktionelleGruppen Thioether.svg

硫醚有机硫化合物的一种,通式为,其中是有机基团。与其他含硫化合物类似,挥发性的硫醚大多具有腐烂的气味。[1]

硫醚的结构类似于,只是原子替换了;由于氧、硫同为氧族元素硫醚也有很多共同性质。硫醚的结构可见于生物分子蛋氨酸辅酶生物素中。

制备

R-Br + HS-R' → R-S-R' + HBr

可催化此类反应,机理是生成了亲核性更强的硫醇盐。

R-CH=CH2 + HS-R' → R-CH2-CH2-S-R'

反应

  • 与相对稳定的醚相比,硫醚(R-S-R)容易被氧化为亚砜(R-S(=O)-R),进一步氧化则得(R-S(=O)2-R)。比如,二甲基硫醚的氧化反应如下:
S(CH3)2 + O → OS(CH3)2
OS(CH3)2 + O → O2S(CH3)2

常用的氧化剂有过氧化氢有机过氧化物次氯酸钠高碘酸钠、亚碘酰苯等。[2]

R3C + R1S-SR2 → R3CSR1 + R2S
  • 三烷基盐与亲核试剂反应,二烷基硫醚作为离去基团离去:
Nu + R3S+ → Nu-R + R-S-R

以上反应在生物学中是转移烷基的方法之一,例如生物体SN2反应S-腺苷基蛋氨酸即扮演甲基化试剂的角色。

  • 与醚不同,硫醚发生S-烷基化生成很稳定的盐,如下例中的三甲基锍:
S(CH3)2 + CH3I → [S(CH3)3]+I

噻吩

五元杂环化合物噻吩在形式上属于硫醚,但由于芳香性的缘故,硫的非键电子在共轭系统中离域,不再具有硫醚中强亲核性孤对电子的特点,因此噻吩很少表现硫醚特征,而且具甜味。对噻吩氢化,得到四氢噻吩C4H8S,芳香性被破坏,分子又恢复了硫醚的典型性质。

参考资料

  1. ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
  2. ^ Michel Madesclaire. Tetrahedron Report Number 210 - Synthesis of sulfoxides by oxidation of thioethers. Tetrahedron, 1986. 42 (20): 5459-5495. doi:10.1016/S0040-4020(01)88150-3
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硫醚
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