104680-74-2Relevant academic research and scientific papers
X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES. PART 28. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES. BACKGROUND AND REACTION OF AMINES WITH BIFUNCTIONAL KETONES.
Ardill, Harriet,Dorrity, M. J. R.,Grigg, Ronald,Leon-Ling, Mooi-Sin,Malone J. F.,et al.
, p. 6433 - 6448 (2007/10/02)
The reaction of isatin, ninhydrin and acenaphtenequinone with primary and secondary amines gives rise to stereospecific formation of intermediate azomethine ylides which can be trapped by cycloaddition to methyl acrylate or N-methylmaleimide.The regiochemistry of the cycloadditions to methyl acrylate is controlled by both frontier orbital and steric interactions with the latter dominating in the examples studied.
Iminium Ion Route to Azomethine Ylides from Primary and Secondary Amines
Ardill, Harriet,Grigg, Ronald,Sridharan, Visuvanathar,Surendrakumar, Sivaguanasundram,Thianpatanagul, Sunit,Kanajun, Saratoon
, p. 602 - 604 (2007/10/02)
Iminium ion formation between primary or secondary amines and carbonyl compounds containing the moiety O=C-C=X results in a facile and stereospecific generation of azomethine ylides which can be trapped in 1,3-dipolar cycloaddition reactions.
