Synthesis and structural studies of <Emphasis Type="Italic">tris</Emphasis>-2-chlorobenzylamine and <Emphasis Type="Italic">tris</Emphasis>-2-bromobenzylamine |
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Authors: | Qing?Chen Carrie?E?Buss Jr" target="_blank">Victor?G?YoungJr Email author" target="_blank">Stephen?FoxEmail author |
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Institution: | (1) Department of Chemistry, University of Louisiana at Monroe, Monroe, Louisiana, 71209-0530;(2) Department of Chemistry, University of Minnesota, Minneapolis, Minnesota, 55455 |
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Abstract: | The tris-2-chloro and 2-bromotribenzylamines are prepared from aqueous ammonia and 2-chlorobenzyl chloride and 2-bromobenzyl bromide, respectively, in ethanol. Recrystallization yielded colorless cubes of each product. The crystal structures are each solved in space group P
, and are isostructural. The tris-2-chloro compound, 1, has a = 7.4226(5) Å, b = 9.0825(7) Å, c = 14.529(1) Å, = 78.279(1) , = 82.389(1) , = 84.661(1) , and V = 948.41(12) Å3 with Z = 2, and dcalc = 1.368 Mg/m3. The tris-2-bromo analog, 2, has a = 7.6569(11) Å, b = 9.0922(13) Å, c = 14.614(2) Å, = 79.286(2) , = 81.777(2) , = 85.401(2) , and V = 987.9(2) Å3 with Z = 2, and dcalc = 1.762 Mg/m3. Lithium–halogen exchange experiments conducted in tetrahydrofuran at –78 C using n-butyl lithium revealed that no exchange occurred for the tris-2-chloro compound, but did occur for the tris-2-bromo analog to yield tribenzylamine upon quench and work-up. |
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Keywords: | Tribenzylamine triclinic 2-chloro 2-bromo lithium– halogen exchange |
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