136409-28-4Relevant articles and documents
N-Vinylketenimines
Capuano, Lilly,Braun, Claudia,Kuehn, Frank
, p. 15 - 18 (2007/10/02)
The title compounds 5 are generated in situ from N-vinyliminotriphenylphosphoranes 1 and ketenes 2 in a Wittig-type reaction.The phosphoranes are useful intermediates for the preparation of numerous heterocycles as illustrated by the formation of 1,3-oxazines 8, pyridinones 9, pyrimidinones 10 and 1,3-thiazines 11.Water adds readily to 5 to yield vinylacetamides 7, whereas thermal rearrangement gives rise to the isoquinoline 4 or the spiro system 6, respectively.Under very mild conditions, crystalline precursors (type 3) of the N-vinylketenimines, which still contain the triphenylphosphonio group, have been isolated.These react like the N-vinylketenimines generated in situ, giving however less byproducts. Key Words: Phosphorus ylides / Ketenes / Ketenimines