ChemicalBook CAS DataBase List Tetraallyltin

Tetraallyltin synthesis

9synthesis methods

Product Name:Tetraallyltin
CAS Number:7393-43-3
Molecular formula:C12H20Sn
Molecular Weight:283

Tetraallyltin is synthesized by the reaction of Allylmagnesium Bromide with Tin(IV) Chloride in THF.

7646-78-8 Synthesis

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1730-25-2
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7393-43-3
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Yield: 89%

Reaction Conditions:

in diethyl ether at -78 - 20; for 2 h;Inert atmosphere;

Steps:

4.1.1 Tetraallylstannane
In a 1 L round-bottomed flask equipped with a magnetic stirrer, dropping funnel, and an argon inlet/outlet an ethereal solution of allylmagnesium bromide (470 mL, 0.75 M, 352 mmol) was placed (under argon). The solution was cooled to -78 °C and, while vigorously stirred, tin(IV) chloride (8.60 mL, 74 mmol) was added dropwise (within ca. 10 min). After the addition was completed, the mixture was allowed to warm to rt (within 1 h) and stirring was continued for 1 h (1.5 h in temp above 0 °C in total). The mixture was then cooled again to -78 °C and satd aq NH₄Cl (94 mL) was added dropwise. The mixture was allowed to warm to rt. The solution was decanted from the semi-crystalline mass, dried, and filtered through Celite. The reaction vessel, the drying agent, and the Celite were washed consecutively with ether (50 mL). The ethereal solutions were combined and the solvent was evaporated. The residue (20.5 g) was distilled collecting fraction at 75 °C/2.5 mmHg. The title product was obtained (colorless liquid, 18.57 g, 89% yield). ¹H NMR in agreement with that previously reported.²⁹

References:

Michalak, Karol;Wicha, Jerzy [Tetrahedron,2014,vol. 70,# 34,p. 5073 - 5081]

7646-78-8 Synthesis

7646-78-8
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