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Thermal reaction of Ru3(CO)12 with alkynyl ketones PhCCC(O)R (RPh (1); 2-Cl-Ph (2); 4-NO2-Ph (3); 2-NH2-Ph (4); and 2-CH3COO-Ph (5)) proceeds in toluene with the formation of Ru3(CO)9(μ-CO)(η4-triruthenium) derivatives (1a–5a), Ru(CO)3(η4-ruthenole) derivatives (1b–4b, 1c–5c and 4d) and cyclotrimerization products (1e–2e and 1f–3f). Compounds 1a–5a were isolated from the reaction of Ru3(CO)12 with one equivalent of 1–5, respectively. Ruthenoles 1b–3b and 1c–3c were collected by adding 1–3 to the corresponding 1a–3a in a molar ratio of 1 : 1. Cyclotrimerization products 1e–2e and 1f–3f were obtained when 1–3 were added to their corresponding 1b–2b and 1c–3c, respectively. 4b, 4c and 4d were afforded during the reaction of 4 with 4a, but only 5c was collected during the reaction of 5 with 5a. All compounds were characterized by NMR, FT-IR, and MS-ESI and most of them were structurally confirmed by single crystal X-ray diffraction. The results suggest that electronic and steric effects of the substituents in the phenyl ring of 1,3-diphenylprop-2-yn-1-one play important roles in regulating the reaction pathways. An electron-withdrawing group is beneficial to the formation of b, c and further formation of e and f; an electron-donating group favors the production of ruthenoles b, c and d, but disfavors the formation of e and f; a substituent with large steric-hindrance prefers only the formation of c.

Electronic and steric effects of substituents in 1,3-diphenylprop-2-yn-1-one during its reaction with Ru3(CO)12

Electronic and steric effects of substituents in 1,3-diphenylprop-2-yn-1-one during its reaction with Ru₃(CO)₁₂