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Generation and Rearrangements of Ylides from Tertiary Amines and α‐Diazo Ketones − Very High Catalytic Activity of [RuCl(η 5 ‐C 5 H 5 )(PPh 3 ) 2 ]
Author(s) -
Del Zotto Alessandro,
Baratta Walter,
Miani Francesca,
Verardo Giancarlo,
Rigo Pierluigi
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200011)2000:22<3731::aid-ejoc3731>3.0.co;2-9
Subject(s) - chemistry , diazo , amine gas treating , catalysis , molar ratio , nitrogen , medicinal chemistry , ylide , organic chemistry
The reaction of N,N ‐dimethyl‐2‐propen‐1‐amine, N , N ‐dimethylbenzylamine and N , N ‐dimethyl‐2‐propyn‐1‐amine with the α‐diazo ketones N 2 CHCOR [R = Me ( 2a ), Et ( 2b ), n Pr ( 2c ), i Pr ( 2d ), (CH 2 ) 10 Me ( 2e ), (CH 2 ) 14 Me ( 2f ) or Ph ( 2g )] in a 1:1 molar ratio, catalysed by the complex [RuCl(η 5 ‐C 5 H 5 )(PPh 3 ) 2 ] ( 1 ) (1% mol), have been investigated. Noticeably, the corresponding α‐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, 1 H and 13 C 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.