104680-80-0Relevant academic research and scientific papers
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 (1986)
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.
X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES. PART 29. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES. REACTION OF CYCLIC SECONDARY AMINES WITH MONO- AND BI- FUNCTIONAL ALDEHYDES
Ardill, Harriet,Fontaine, Xavier L. R.,Grigg, Ronald,Henderson, Deirdre,Montgomery, John,et al.
, p. 6449 - 6466 (2007/10/02)
1,2,3,4-Tetrahydro-isoquinoline and -β-carboline react with a range of mono- and bi- functional aldehydes to give azomethine ylides.The anti-dipole is formed stereospecifically or, in the case of benzaldehyde and 2-methylbenzaldehyde, stereoselectively.The effect of the structure of the aldehyde on the stereochemistry of the derived azomethine ylide is rationalised in terms of steric and electronic effects.Inter- and intra-molecular trapping of the azomethine ylides gives cycloadducts in good yield.
