Regioselective hydrocarbonylation of phenylacetylene to α,β-unsaturated esters and thioesters with Fe(CO)5and Mo(CO)6
A highly regioselective hydrocarbonylation of phenylacetylene with thiols and alcohols was developed using metal carbonyls/diazabicyclo[2.2.2]octane (DABCO) system at 100?°C in DMF. The use of Mo(CO)6and thiols in the presence of DABCO was applied as an efficient Pd-free method for hydrothiocarbonylation of phenylacetylene into trans-α,β-cinamyl thioesters in excellent yields (88–98%). Similar reaction using Fe(CO)5/ROH/DABCO system resulted into high yield synthesis of trans-α,β-cinamyl esters (87–98%). These reactions were conducted under mild reaction conditions without the need to use gaseous CO or any phosphine ligand and palladium catalyst.
The authors examine methods of synthesis and the properties of 2-vinyloxyethyl acylates, a little-studied class of organic compounds on which literature information is very limited and which are of interest as possible monomers for synthesis of macromolecular compounds and as synthetic models of natural physiologically active substances. Methods have been devised for synthesis of 2-vinyloxyethyl acylates - potential monomers for synthesis of macromolecular and physiologically active compounds. The structural characteristics of the synthesized compounds were studied. Cationic polymerization of 2-vinyloxyethyl acylates was carried out, and the dependence of the reaction rate and of the properties of the resultant oligomers on the nature of the acyl radical was determined.
Mikhant'eva,Romanova,Mikhan'tev
p. 1017 - 1022
(2007/10/02)
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