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Highly selective synthesis of (E)-N-aryl-N-(1-propenyl) ethanamides via isomerization of N-allyl ethanamides catalyzed by ruthenium complexes

✍ Scribed by Stanislaw Krompiec; Mariola Pigulla; Wojciech Szczepankiewicz; Tadeusz Bieg; Nikodem Kuznik; Katarzyna Leszczynska-Sejda; Maciej Kubicki; Teresa Borowiak

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 115 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01457-5

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✦ Synopsis

A convenient and highly selective method of synthesis of (E)-N-aryl-N-(1-propenyl)ethanamides via isomerization of respective N-allyl-N-arylethanamides catalyzed by [RuClH(CO)(PPh 3 ) 3 ] has been described. N-Allyl-N-arylethanamides have been obtained by allylation of respective N-arylethanamides under PTC conditions. It is proposed that the observed selectivity of the double bond migration to (E)-enamides is due to the interaction of the arene ring with the Ru atom in the transition state.

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