Abstract
Molybdenum(V) starting material, (PyH) 5 [Mo V OCl 4 (H 2 O)] 3 Cl 2 , reacted in acetonitrile with 3-phenyllactic acid (2-hydroxy-3-phenylpropanoic acid) in the presence of tetraphenylphosphonium counterions to {(C 6 H 5 ) 4 P} 2 [(Mo VI O 2 Cl 2 ) 2 (C 2 O 4 )] (C 2 O 4 2− = oxalate anion). By the X-ray structure analysis of the product, the oxidation of the metal to + 6 oxidation state and the oxidative cleavage of 3-phenyllactic acid to oxalate ion were undoubtedly confirmed. Several other products of the transformation of the organic substrate were identified by 1 H NMR spectroscopy: phenylacetic acid, benzaldehyde, phenylacetaldehyde and lactone, 3,4-diphenyl-2,5-dihydrofuran-2-one. 3-phenyllactic acid undergoes in the presence of molybdenum(V) species a series of transformation reactions which produce oxalate, benzaldehyde, phenylacetaldehyde, phenylacetic acid and 3,4-diphenyl-2,5-dihydrofuran-2-one. ► Oxidation products of 3-phenyllactic acid. ► Oxidation of α -hydroxycarboxylic acids. ► Coordination chemistry of molybdenum and α -hydroxycarboxylic acids. ► X-ray structure of {(C 6 H 5 ) 4 P} 2 [(MoO 2 Cl 2 ) 2 (C 2 O 4 )].
Published Version
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