氫化三丁基錫

氫化三丁基錫
Skeletal formula of tributyltin with one explicit hydrogen added	Spacefill model of tributyltin
	系統名; Tributylstannane
識別
CAS號	688-73-3
PubChem	5948
ChemSpider	5734
SMILES	CCCC[SnH](CCCC)CCCC;
Beilstein	3587329
Gmelin	4258
EINECS	211-704-4
ChEBI	27086
MeSH	Tributyltin
性質
化學式	SnC; 12H; 28
摩爾質量	291.06 g mol−1 g·mol⁻¹
密度	1.082 g cm−3
沸點	80 °C（353 K）
溶解性（水）	緩慢分解
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

氫化三丁基錫 是一種有機錫化合物，化學式 (C₄H₉)₃SnH。它是一種無色液體，可溶於有機溶劑。這種化合物是有機合成里，氫原子的來源。

製備和特徵[編輯]

氫化三丁基錫可以由氧化三丁基錫（英語：Tributyltin oxide）被聚甲基氫硅氧烷還原而成 (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

氫化物是一種可蒸餾的液體，對空氣有輕微的敏感，會分解成(Bu₃Sn)₂O。其紅外光譜在ν_Sn-H的1814cm^-1處顯示很強的能帶。

應用[編輯]

它是有機合成里是一種有用的試劑。它和偶氮二異丁腈 (AIBN) 混合或被光照時，氫化三丁基錫會將有機鹵化物（和相關基團）轉化為相應的烴。此過程是通過涉及自由基Bu₃Sn•的自由基反應機製發生的。 ^[4]^[5] 該基團從另一個氫化三丁基錫分子中奪取H•，從而傳播該鏈。氫化三丁基錫作為H•供體的用途可歸因於其相對較弱的鍵強（78 kcal/mol）。 ^[6]

它是氫錫基化（英語：Hydrostannylation）反應的選擇性試劑： ^[7]

RC₂R' + HSnBu₃ → RC(H)=C(SnBu₃)R'

參見[編輯]

擴展閱讀[編輯]

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

參考資料[編輯]

^ SnBu3H - PubChem Public Chemical Database. The PubChem Project. USA: National Center for Biotechnology Information. [2020-08-23]. （原始內容存檔於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 （頁面存檔備份，存於網際網路檔案館）, 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]. （原始內容存檔於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 （頁面存檔備份，存於網際網路檔案館）, 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.

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