1-(1,3-Benzothiazol-2-ylsulfanyl)propan-2-olate anion as a potential multifunctional ligand in aluminum complexes

Basiak, Dariusz; Ochal, Zbigniew; Justyniak, Iwona; Ziemkowska, Wanda

doi:10.1016/j.poly.2015.10.048

Cited by 5 publications

(1 citation statement)

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“…The central Al 2 O 2 rings are similar to that of typical alkoxides of group 13 metal alkyls obtained in reactions of R 3 M (R = Me, Et, i -Bu; M = Al, Ga) with diverse monoalcohols [ 41 , 42 , 43 ]. The bond lengths C(1)-C(2) [1.533(2) Å in 2aa ] C(7)-C(8) [1.533(2) Å in 2ab ], C(1)-C(8) [1.534(2) Å in 2ba ], C(5)-C(12) [1.538(2) Å in 2bb ] and C(6)-C(13) [1.533(4) Å in 3bb ] are typical for single C–C bonds, which proves the transformation of the C=C double bonds in the β-keto sulfones into single C–C bonds in the appropriate β-hydroxy sulfone residues.…”

Section: Resultsmentioning

confidence: 62%

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

et al. 2022

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β-Hydroxy sulfones are important in organic synthesis. The simplest method of β-hydroxy sulfones synthesis is the hydrogenation of β-keto sulfones. Herein, we report the reducing properties of alkyl aluminum compounds R3Al (R = Et, i-Bu, n-Bu, t-Bu and n-Hex); i-Bu2AlH; Et2AlCl and EtAlCl2 in the hydrogenation of β-keto sulfones. The compounds i-Bu2AlH, i-Bu3Al and Et3Al are the at best reducing agents of β-keto sulfones to β-hydroxy sulfones. In reactions of β-keto sulfones with aluminum trialkyls, hydroalumination products with β-hydroxy sulfone ligands [R2AlOC(C6H5)CH2S(O)2(p-R1C6H4]n [where n = 1,2; 2aa: R = i-Bu, R1 = CH3; 2ab: R = i-Bu, R1 = Cl; 2ba: R = Et, R1 = CH3; 2bb: R = Et, R1 = Cl] and {[Et2AlOC(C6H5)CH2S(O)2(p-ClC6H4]∙Et3Al}n3bb were obtained. These complexes in the solid state have a dimeric structure, while in solutions, they appear as equilibrium monomer–dimer mixtures. The hydrolysis of both the isolated 2aa, 2ab, 2ba, 2bb and 3bb and the postreaction mixtures quantitatively leads to pure racemic β-hydroxy sulfones. Hydroalumination reaction of β-keto sulfones with alkyl aluminum compounds and subsequent hydrolysis of the complexes is a simple and very efficient method of β-hydroxy sulfones synthesis.

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Section: Resultsmentioning

confidence: 62%

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

et al. 2022

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Aminophenolates of aluminium, gallium and zinc: Synthesis, characterization and polymerization activity

Basiak

Socha

Rzepiński

et al. 2017

Applied Organom Chemis

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Complexes containing aminophenolate ligands are considered as very efficient initiators of ring‐opening polymerization (ROP). Our systematic studies of the reactions of two selected aminophenols, 2‐[(p‐tolylamino)methyl]‐4‐(2,4,4‐trimethylpentan‐2‐yl)phenol (L'H2) and 2‐cyclohexylaminomethyl‐4‐methylphenol (L″H2), with alkyl compounds of aluminium, gallium and zinc resulted in the formation of a variety of products depending on the type of metallic centre and alkyl groups bonded to metal atoms. New trinuclear aluminium complexes (Me5Al3(L′)2 (1) and Me5Al3(L″)2 (2)), monomeric aluminium (tBu2Al(L'H) (3) and tBu2Al(L″H) (5)) and gallium (tBu2Ga(L'H) (4) and tBu2Ga(L″H) (6)) compounds, and dinuclear gallium (Et2Ga(L″H)·Et3Ga (7)) and zinc (tBuZn(L″H)]2 (8)) complexes were isolated and characterized. The molecular and crystal structures of 7 and 8 were determined on the basis of an X‐ray diffraction study. Polymerization tests showed that only three complexes (6–8) had activity in the ROP of ε‐caprolactone, whereas 1–5 were inactive in ROP.

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Reactivity of a benzothiazole-thiourea derivative with the oxorhenium(V) core: Isolation of rhenium(III) and (V) complexes

et al. 2016

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1-(1,3-Benzothiazol-2-ylsulfanyl)propan-2-olate anion as a potential multifunctional ligand in aluminum complexes

Cited by 5 publications

References 54 publications

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

Aminophenolates of aluminium, gallium and zinc: Synthesis, characterization and polymerization activity

Reactivity of a benzothiazole-thiourea derivative with the oxorhenium(V) core: Isolation of rhenium(III) and (V) complexes

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