K. Osakada, T. Ikariya, S. Yoshikawa
May 11, 1982
Citations
0
Influential Citations
53
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Reactions of Five-membered cyclic dicarboxylic anhydrides, such as phthalic anhydride and succinic anhydride, with RuH2(PPh3)3] and 3-formyl propionate [RuH(OCOCH2CH2CHO)(PPh3)3], via the CO bond cleavage of the anhydrides. Similar reactions of methylsuccinic anhydride or ethylsuccinic anhydride with RuH2(PPh3)4 afford mixtures of the isomers [RuH(OCOCHRCH2CHO)(PPh3)3] and RuH(OCOCH2CHRCHO)(PPh3)3] (R CH3 or C2H5), in ca. 3 to 1 molar ratio in each reaction. Complexes with 2-acyl benzoate or 3-acyl propionate ligands formulated as [RuH(o-OCOC6H4COCH3(PPH3)3] or [RuH(OCOCH2CH2COR/t')(PPh3)3](R/t' CH3, C6H5) are prepared from the reaction of corresponding 2-acyl benzoic or 3-acyl propionic acids with RuH2(PPh3)4. Upon contact with hydrogen at elevated pressure, or with hydrogen chloride or carbon monoxide at atmospheric pressure, these complexes release the corresponding γ-lactones, which are formed through the reduction of formyl or acyl groups in the carboxylate ligands followed by intramolecular condensations. Hydrogenation of 3-acyl propionic acids using ruthenium(II) complexes as catalyst gives γ-substituted γ-lactones in high yields.