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Hydrolysis of C , N ‐chelated diorganotin(IV) chlorides and catalysis of transesterification reactions
Author(s) -
Padělková Zdeňka,
Weidlich Tomáš,
Císařová Ivana,
Růžička Aleš
Publication year - 2009
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.1507
Subject(s) - chemistry , hydrolysis , transesterification , catalysis , diastereomer , chelation , sodium hydroxide , hydroxide , medicinal chemistry , aqueous solution , ligand (biochemistry) , stereocenter , benzene , organic chemistry , nuclear chemistry , enantioselective synthesis , biochemistry , receptor
Diorganotin(IV) dichlorides of formula L CN RSnCl 2 (where R is n Bu or Ph) containing one L CN chelating ligand were hydrolyzed with aqueous sodium hydroxide in benzene. The composition of the products is strongly dependent on the amount of hydroxide. The partially hydrolyzed compounds of composition (L CN RSnCl) 2 (µ‐O) were isolated as crystalline products. A hydrolysis where more than one molar equivalent of NaOH is employed gave only a mixture of unidentifiable products. The structure of (L CN PhSnCl) 2 (µ‐O) was determined by X‐ray diffraction techniques in the solid state. In solution there was a mixture of diastereoisomers found, where the tin atoms serve as a stereogenic centers. The catalytic activity of starting dichlorides as well as (L CN PhSnCl) 2 (µ‐O) in various transesterification processes was investigated. The activity is very low in the case of starting dichlorides. When two molar equivalents of NaH are added or (L CN PhSnCl) 2 (µ‐O) is employed in the catalytic experiments, the activity is comparable to the literature data. Copyright © 2009 John Wiley & Sons, Ltd.