107556-36-5Relevant academic research and scientific papers
Spectroscopic studies on the structure and conformation of Lewis acid-aldehyde complexes
Denmark, Scott E.,Almstead, Neil G.
, p. 3133 - 3139 (1993)
The complexation of aldehydes with SnCl4 and BF3 has been studied spectroscopically. It was determined by HOESY analysis that the aldehyde-SnCl4 complexes examined prefer the E geometry. This preferential complexation is likely due to steric influences from the substituents on the aldehyde. A qualitative assessment of the relative basicity of various substituted aldehydes was also determined. It was found that both 2-heptynal and n-heptanal were significantly weaker Lewis bases than either (E)-2-heptenal or 4-terf-butylbenzaldehyde. The difference in basicity between (E)-2-heptenal and 2-heptynal is thought to arise from the electronegativity of the sp carbon atom. Finally the conformation of Lewis acid completed and neutral (E)-2-heptenal was studied in solution. When complexed to either BF3 or SnCl4 or even uncomplexed, (E)-2-heptenal was determined by 1D-NOE studies to be in the s-trans conformation.
