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Enamides via Long‐Distance Migration of Double Bonds
Author(s) -
Sergeyev Sergey A.,
Hesse Manfred
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390074
Subject(s) - chemistry , isomerization , double bond , yield (engineering) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
A new method for preparation of enamides ( N ‐(alken‐1‐yl) amides) by means of the ‘long‐distance' migration of the double bond in unsaturated amides in the presence of [Fe(CO) 5 ] is described. The method is shown to be particularly useful for the isomerization of N ‐(but‐3‐enyl)amides, while, in the case of N ‐(pent‐4‐enyl) and N ‐(hex‐5‐enyl) amides the mixture of products was formed and the yield of the enamide was relatively low.