Ru3(CO)12 (1) and Ru(CO)3(PPh3)2 (2) catalyze the reductive carbonylation of nitrobenzene and of substituted aromatic mononitro compounds to give the corresponding methylcarbamates, in toluene-methanol, at 160-170 °C and 60 atm, with high selectivity, in the presence of NEt4+Cl- as cocatalyst. Compound 1 also catalyzes the conversion of 2,4-dinitrotoluene into the corresponding dicarbamate although less efficiently. The effects of CO pressure, reaction temperature, and amount and nature of the added alcohol and cocatalyst have been studied. The mechanism of the reaction catalyzed by 1 has been investigated by studying the reactivity and catalytic activity of possible intermediates.
RUTHENIUM CARBONYL CATALYZED REDUCTIVE CARBONYLATION OF AROMATIC NITRO-COMPOUNDS - A SELECTIVE ROUTE TO CARBAMATES / S. CENINI, C. CROTTI, M. PIZZOTTI, F. PORTA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 53:6(1988), pp. 1243-1250.
RUTHENIUM CARBONYL CATALYZED REDUCTIVE CARBONYLATION OF AROMATIC NITRO-COMPOUNDS - A SELECTIVE ROUTE TO CARBAMATES
S. CENINI;M. PIZZOTTI;F. PORTA
1988
Abstract
Ru3(CO)12 (1) and Ru(CO)3(PPh3)2 (2) catalyze the reductive carbonylation of nitrobenzene and of substituted aromatic mononitro compounds to give the corresponding methylcarbamates, in toluene-methanol, at 160-170 °C and 60 atm, with high selectivity, in the presence of NEt4+Cl- as cocatalyst. Compound 1 also catalyzes the conversion of 2,4-dinitrotoluene into the corresponding dicarbamate although less efficiently. The effects of CO pressure, reaction temperature, and amount and nature of the added alcohol and cocatalyst have been studied. The mechanism of the reaction catalyzed by 1 has been investigated by studying the reactivity and catalytic activity of possible intermediates.
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