Reactions of β-keto sulfones with t-butyl aluminum compounds: Reinvestigation of tri-t-butyl aluminum synthesis

Tomasz Wojciechowski , Zbigniew Ochal , P. Socha , Ł. Dobrzycki , Wanda Ziemkowska

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.
Author Tomasz Wojciechowski (FC / DCOC)
Tomasz Wojciechowski,,
- Department Of Catalysis And Organometallic Chemistry
, Zbigniew Ochal (FC / CDSB)
Zbigniew Ochal,,
- Chair of Drug and Cosmetics Biotechnology
, P. Socha - Faculty of Chemistry (WChUW) [University of Warsaw (UW)]
P. Socha,,
-
, Ł. Dobrzycki - Faculty of Chemistry (WChUW) [University of Warsaw (UW)]
Ł. Dobrzycki,,
-
, Wanda Ziemkowska (FC / DCOC)
Wanda Ziemkowska,,
- Department Of Catalysis And Organometallic Chemistry
Journal seriesApplied Organometallic Chemistry, ISSN 0268-2605, e-ISSN 1099-0739, [1099-0739]
Issue year2020
Pages1-9
Publication size in sheets0.5
ASJC Classification1600 General Chemistry; 1604 Inorganic Chemistry
DOIDOI:10.1002/aoc.5961
URL https://onlinelibrary.wiley.com/doi/full/10.1002/aoc.5961
Languageen angielski
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 25-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 0.676; WoS Impact Factor: 2018 = 3.259 (2) - 2018=3.013 (5)
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