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The ruthenium(II) half-sandwich complex [RuCl(η 5 -C 5 H 5 )(PPh 3 ) 2 ] (1) catalyses the reaction between methanol and alkylamines RNH 2 or R 1 R 2 NH to afford RN(CH 3 ) 2 and R 1 R 2 NCH 3 products, respectively. The reaction is quantitative and generally fast, at the methanol reflux temperature, for a wide spectrum of substrates. Starting from primary amines, the stepwise formation of RN=CH 2 , RNHCH 3 , and

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A catalytic amount of [RuCl(η 5 -C 5 H 5 )(PPh 3 ) 2 ] (1) (0.1 mol-%) at 60°C stereoselectively decomposes α-diazo carbonyl compounds N 2 CHCOR [R = EtO, Me, Et, nPr, iPr, Ph, (CH 2 ) 10 Me, and (CH 2 ) 14 Me] affording quantitatively RCOCH=CHCOR carbene dimers [R = EtO (10), Me (11), Et (12), nPr (13), iPr (14), Ph (15), (CH 2 ) 10 Me (16), and (CH 2 ) 14 Me (17)]. The cis isomer is formed in 95−99% purity, depending on the R group. Under the same experimental conditions, N 2 CHCOR 1 and N 2 CHCOR 2 react in equimolar amounts to give mixtures of unsymmetrical cis-R 1 COCH=CHCOR 2 (18−32), and symmetrical cis-R 1 COCH=CHCOR 1 and cis-R 2 COCH=CHCOR 2 alkenes. The unsymmetrical cis-alkenes 23−32 are formed [a]