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Reactions of β ‐keto sulfones with t ‐butyl aluminum compounds: Reinvestigation of tri‐ t ‐butyl aluminum synthesis
Author(s) -
Wojciechowski Tomasz,
Ochal Zbigniew,
Socha Paweł,
Dobrzycki Łukasz,
Ziemkowska Wanda
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5961
Subject(s) - chemistry , sulfone , medicinal chemistry , stereochemistry , organic chemistry
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 ‐Bu 3 Al·OEt 2 with [ p ‐RC 6 H 4 S(O) 2 C(H) 2 C(Ph) = O] (where R = CH 3 , 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 ‐RC 6 H 4 S(O 2 )C(H) = C (Ph)‐OAl( t ‐Bu) 2 ] [where R = CH 3 ( 2 ); R = Cl ( 4 )] possessing β ‐keto sulfone ligands, complexes with β ‐hydroxy sulfone ligands [ p ‐RC 6 H 4 S(O 2 )C(H) 2 ‐C (Ph)‐OAl( t ‐Bu) 2 ] [where R = CH 3 ( 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 ‐Bu 2 AlH, which is an impurity of t ‐Bu 3 Al. These compounds are obtained, for the first time, as intermediate products in the hydrogenation reaction of β ‐keto sulfones. In this work, during t ‐Bu 3 Al·OEt 2 production t ‐Bu 2 AlH·OEt 2 formed as a by‐product. Re‐examination of reaction conditions of AlCl 3 with t ‐BuMgCl resulted in a control of the t ‐Bu 2 AlH·OEt 2 by‐product content in t ‐Bu 3 Al·OEt 2 .