The reaction of N,N-dimethyl-2-propen-1-amine, N,N-dimethylbenzylamine and N,N-dimethyl-2-propyn-1-amine with the alpha -diazo ketones N2CHCOR [R = Me (2a), Et (2b), nPr (2c), iPr (2d), (CH2)(10)Me (2e), (CH2)(14)Me (2f) or Ph (2g)] in a 1:1 molar ratio, catalysed by the complex [RuCl(eta (5)-C5H5)(PPh3)(2)] (1) (1% mel), have been investigated. Noticeably, the corresponding alpha -amino ketones 3a-g, 4a-g and 5a-g are readily and quantitatively formed by rearrangement of transient nitrogen ylides. Compounds 3-5, most of which have not yet been reported, have been isolated and fully characterised by IR, H-1 and C-13 NMR spectroscopy and GC-MS. It has been proved that complex 1 is an excellent and specific catalyst for the generation of nitrogen ylides from diazo carbonyls.
Generation and Rearrangements of Ylides from Tertiary Amines and alpha-Diazo Ketones - Very High Catalytic Activity of [RuCl(h5-C5H5)(PPh3)2]
DEL ZOTTO, Alessandro;BARATTA, Walter;VERARDO, Giancarlo;RIGO, Pierluigi
2000-01-01
Abstract
The reaction of N,N-dimethyl-2-propen-1-amine, N,N-dimethylbenzylamine and N,N-dimethyl-2-propyn-1-amine with the alpha -diazo ketones N2CHCOR [R = Me (2a), Et (2b), nPr (2c), iPr (2d), (CH2)(10)Me (2e), (CH2)(14)Me (2f) or Ph (2g)] in a 1:1 molar ratio, catalysed by the complex [RuCl(eta (5)-C5H5)(PPh3)(2)] (1) (1% mel), have been investigated. Noticeably, the corresponding alpha -amino ketones 3a-g, 4a-g and 5a-g are readily and quantitatively formed by rearrangement of transient nitrogen ylides. Compounds 3-5, most of which have not yet been reported, have been isolated and fully characterised by IR, H-1 and C-13 NMR spectroscopy and GC-MS. It has been proved that complex 1 is an excellent and specific catalyst for the generation of nitrogen ylides from diazo carbonyls.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
