氢化三丁基锡

氢化三丁基锡
Skeletal formula of tributyltin with one explicit hydrogen added	Spacefill model of tributyltin
	系统名; Tributylstannane
识别
CAS号	688-73-3
PubChem	5948
ChemSpider	5734
SMILES	CCCC[SnH](CCCC)CCCC;
Beilstein	3587329
Gmelin	4258
EINECS	211-704-4
ChEBI	27086
MeSH	Tributyltin
性质
化学式	SnC; 12H; 28
摩尔质量	291.06 g mol−1 g·mol⁻¹
密度	1.082 g cm−3
沸点	80 °C（353 K）
溶解性（水）	缓慢分解
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

氢化三丁基锡 是一种有机锡化合物，化学式 (C₄H₉)₃SnH。它是一种无色液体，可溶于有机溶剂。这种化合物是有机合成里，氢原子的来源。

制备和特征

氢化三丁基锡可以由氧化三丁基锡（英语：Tributyltin oxide）被聚甲基氢硅氧烷还原而成 (Bu = CH₃CH₂CH₂CH₂)：^[2]^[3]

2"(MeSiH)" + (Bu₃Sn)₂O → "(Me₂Si)₂O" + 2 Bu₃SnH

(Bu₃Sn)₂O + 2/n (MeSi(H)O)_n → 2 Bu₃SnH + 1/n [(MeSiO)₂O]_n

氢化物是一种可蒸馏的液体，对空气有轻微的敏感，会分解成(Bu₃Sn)₂O。其红外光谱在ν_Sn-H的1814cm^-1处显示很强的能带。

应用

它是有机合成里是一种有用的试剂。它和偶氮二异丁腈 (AIBN) 混合或被光照时，氢化三丁基锡会将有机卤化物（和相关基团）转化为相应的烃。此过程是通过涉及自由基Bu₃Sn•的自由基反应机制发生的。 ^[4]^[5] 该基团从另一个氢化三丁基锡分子中夺取H•，从而传播该链。氢化三丁基锡作为H•供体的用途可归因于其相对较弱的键强（78 kcal/mol）。 ^[6]

它是氢锡基化（英语：Hydrostannylation）反应的选择性试剂： ^[7]

RC₂R' + HSnBu₃ → RC(H)=C(SnBu₃)R'

参见

扩展阅读

Hayashi, K.; Iyoda, J.; Shiihara, I. "Reaction of organotin oxides, alkoxides and acyloxides with organosilicon hydrides. New preparative method of organotin hydrides " J. Organomet. Chem. 1967, 10, 81. doi:10.1016/S0022-328X(00)81719-2

参考资料

^ SnBu3H - PubChem Public Chemical Database. The PubChem Project. USA: National Center for Biotechnology Information. [2020-08-23]. （原始内容存档于2012-11-03）.
^ Maleczka, Robert E.; Terrell, Lamont R.; Clark, Damon H.; Whitehead, Susan L.; Gallagher, William P.; Terstiege, Ina. Application of Fluoride-Catalyzed Silane Reductions of Tin Halides to the in Situ Preparation of Vinylstannanes. J. Org. Chem. 1999, 64: 5958–5965. doi:10.1021/jo990491+.
^ Tormo, J.; Fu, G. C. α-D-Ribo-hexofuranose, 3-deoxy-1,2:5,6-bis-O-(1-methylethylidene). Org. Synth. 2002, 78: 239. doi:10.15227/orgsyn.078.0239.
^ OUP catalogue page （页面存档备份，存于互联网档案馆）, J. Clayden, N. Greeves, S. Warren and P. Wothers, in Organic Chemistry, 2000, OUP, Oxford, ch. 39, pp. 1040-1041.
^ T. V. (Babu) RajanBabu, Philip C. Bulman Page, Benjamin R. Buckley, "Tri-n-butylstannane" Encyclopedia of Reagents for Organic Synthesis 2004, John Wiley & Sons. doi:10.1002/047084289X.rt181.pub2
^ Laarhoven, L. J. J.; Mulder, P.; Wayner, D.D. M. "Determination of Bond Dissociation Enthalpies in Solution by Photoacoustic Calorimetry" Acc. Chem. Res. 1999, 32, 342 doi:10.1021/ar9703443
^ Smith, Nicholas D.; Mancuso, John; Lautens, Mark. Metal-Catalyzed Hydrostannations. Chemical Reviews. 2000, 100 (8): 3257–3282. PMID 11749320. doi:10.1021/cr9902695.

[1] SnBu3H - PubChem Public Chemical Database. The PubChem Project. USA: National Center for Biotechnology Information. [2020-08-23]. （原始内容存档于2012-11-03）.

[2] Maleczka, Robert E.; Terrell, Lamont R.; Clark, Damon H.; Whitehead, Susan L.; Gallagher, William P.; Terstiege, Ina. Application of Fluoride-Catalyzed Silane Reductions of Tin Halides to the in Situ Preparation of Vinylstannanes. J. Org. Chem. 1999, 64: 5958–5965. doi:10.1021/jo990491+.

[3] Tormo, J.; Fu, G. C. α-D-Ribo-hexofuranose, 3-deoxy-1,2:5,6-bis-O-(1-methylethylidene). Org. Synth. 2002, 78: 239. doi:10.15227/orgsyn.078.0239.

[Clayden-4] OUP catalogue page （页面存档备份，存于互联网档案馆）, J. Clayden, N. Greeves, S. Warren and P. Wothers, in Organic Chemistry, 2000, OUP, Oxford, ch. 39, pp. 1040-1041.

[5] T. V. (Babu) RajanBabu, Philip C. Bulman Page, Benjamin R. Buckley, "Tri-n-butylstannane" Encyclopedia of Reagents for Organic Synthesis 2004, John Wiley & Sons. doi:10.1002/047084289X.rt181.pub2

[6] Laarhoven, L. J. J.; Mulder, P.; Wayner, D.D. M. "Determination of Bond Dissociation Enthalpies in Solution by Photoacoustic Calorimetry" Acc. Chem. Res. 1999, 32, 342 doi:10.1021/ar9703443

[7] Smith, Nicholas D.; Mancuso, John; Lautens, Mark. Metal-Catalyzed Hydrostannations. Chemical Reviews. 2000, 100 (8): 3257–3282. PMID 11749320. doi:10.1021/cr9902695.

[1]

[2]

[3]

[4]

[5]

[6]

[7]