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Towards Extended Zinc Ethylsulfinate Networks by Stepwise Insertion of Sulfur Dioxide into Zn−C Bonds
Author(s) -
Tulewicz Adam,
WolskaPietkiewicz Małgorzata,
Jędrzejewska Maria,
Ratajczyk Tomasz,
Justyniak Iwona,
Lewiński Janusz
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902733
Subject(s) - dabco , chemistry , lewis acids and bases , zinc , hexamethylenetetramine , reactivity (psychology) , medicinal chemistry , toluene , octane , transition metal , polymer chemistry , inorganic chemistry , catalysis , organic chemistry , medicine , alternative medicine , pathology
Abstract The ability to utilize polluting gases in efficient metal‐mediated transformations is one of the most pressing challenges of modern chemistry. Despite numerous studies on the insertion of SO 2 into M−C bonds, the chemical reaction of SO 2 with organozinc compounds remains little explored. To fill this gap, we report here the systematic study of the reaction of Et 2 Zn towards SO 2 as well as the influence of Lewis bases on the reaction course. Whereas the equimolar reaction provided a novel example of a structurally characterized organozinc ethylsulfinate compound of general formula [(EtSO 2 )ZnEt] n , the utilization of an excess of SO 2 led to the formation of the zinc(II) bis(ethylsulfinate) compound [(EtSO 2 ) 2 Zn] n . Moreover, we have discovered that the presence of N‐donor Lewis bases represents an efficient tool for the preparation of extended zinc ethylsulfinates, which in turn led to the formation of 1D [(EtSO 2 ZnEt) 2 (hmta)] n and 2D [((EtSO 2 ) 2 Zn) 2 (DABCO)] n ⋅ solv (in which solv=THF or toluene, hmta= hexamethylenetetramine, and DABCO=1,4‐diazabicyclo[2.2.2]octane) coordination polymers, respectively. The results of DFT calculations on the reactivity of SO 2 towards selected Zn−C reactive species as well as the role of an N‐donor Lewis base on the stabilization of the transition states complement the discussion.