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Reactions of β-keto sulfones with t-butyl aluminum compounds: Reinvestigation of tri-t-butyl aluminum synthesis |
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| Authors: | Tomasz Wojciechowski Zbigniew Ochal Paweł Socha Łukasz Dobrzycki Wanda Ziemkowska |
| Institution: | 1. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw, 00-664 Poland
Contribution: Investigation;2. Department of Chemistry, University of Warsaw, Pasteura 1, Warsaw, 02-093 Poland Contribution: Investigation;3. Department of Chemistry, University of Warsaw, Pasteura 1, Warsaw, 02-093 Poland Contribution: Supervision;4. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw, 00-664 Poland |
| Abstract: | t-Butyl derivatives play a significant role in the organometallic chemistry of group 13 metals. It was shown on the basis of reactions of t-Bu3Al·OEt2 with p-RC6H4S(O)2C(H)2C(Ph) = O] (where R = CH3, Cl) β-keto sulfones that the structure of the reaction products depends on the purity of the aluminum compound used. In the reactions, in addition to the expected complexes p-RC6H4S(O2)C(H) = C (Ph)-OAl(t-Bu)2] where R = CH3 ( 2 ); R = Cl ( 4 )] possessing β-keto sulfone ligands, complexes with β-hydroxy sulfone ligands p-RC6H4S(O2)C(H)2-C (Ph)-OAl(t-Bu)2] where R = CH3 ( 1 ); R = Cl ( 3 )] were formed. Compounds 1 and 3 were the result of the hydroalumination reaction of the β-keto sulfone ligands with t-Bu2AlH, which is an impurity of t-Bu3Al. These compounds are obtained, for the first time, as intermediate products in the hydrogenation reaction of β-keto sulfones. In this work, during t-Bu3Al·OEt2 production t-Bu2AlH·OEt2 formed as a by-product. Re-examination of reaction conditions of AlCl3 with t-BuMgCl resulted in a control of the t-Bu2AlH·OEt2 by-product content in t-Bu3Al·OEt2. |
| Keywords: | hydroalumination hydrogenation tri-t-butyl aluminum β-Hydroxy sulfones β-Keto sulfones |